This story is a work of fiction, and simply a fantasy for your pleasure (Billy if you really are out there I want to know..LOL!). I love to hear from my readers. It is so great to get feedback and connect with people with like interests of all genders. Enjoy!
Mary came into my office and said, "Come on sad sack tonight we are going out on the town. I need a wing-man and you need to get a life!"
She was right. Mary has been my friend since art school. In fact she got me this job at the magazine as staff photographer. She knew I had been down in the dumps since my break-up with my old girl friend, Lauren. Lauren had been my first true relationship since my divorce, and at 38 I was starting to think I was a completely hopeless.
So I agreed and we met at a little bistro for a quick bite before we headed out for the evening. Mary is my best friend, we can talk about anything, and because she is a Lesbian there is no sexual tension between us. We are both interested in girls and she brings a female perspective to the situation. She had not been in a relationship for several months and she made it clear that tonight she intended to "get-some." My wing-man position tonight was clear, but I was happy to tag along and have a few drinks. I wasn't expecting much out of the nights activities.
The first bar we went to was in a word "lame." It was a mellow acoustic music place, people sitting in small groups, sipping white wine. We had a drink and listened to a couple of songs. It was approaching 11:00 pm when Mary said, "let's get out of here before they start to serve the milk and cookies."
We hopped into a cab and Mary told the driver, "5280 Club, please"
I had never heard of the place but I figured Mary knew what she was doing and anything was better than the last club. We arrived at a large black warehouse with an awning in front and two bouncers, a large man and a large woman. The awning simply had the numbers "5280" on the front. There was a line of people waiting to get in but Mary simply walked up to the large woman and gave her a hug and whispered something in her ear. The large woman bouncer laughed and unhooked the velvet rope and let us in. Mary is amazing that way, she knows everybody and the people she doesn't know she can charm.
It took a second for my eyes to adjust to the dark interior. There was the deep bass pulse of house music and a DJ commanded the dance floor from a raised stage. Through out the multi-tiered space dance areas were punctuated by low couches around large round coffee tables, platforms really, and pillars with scantily clad men and women dancers. A large bar ran along one wall and that's where we headed.
It didn't take long to notice that most of the people in the club were in same-sex groups. I squeezed into a spot along the bar and ordered drinks. What I thought was a very tall black woman turned and accidentally bumped into me. Upon seeing her face I noticed that she was not a woman at all but a man in drag. She gave me a smile and a wink and went about her way.
Mary squeezed my arm and gave me a smile. "Careful, Mary said, she would eat you alive."
We both laughed and I bought us a round. We toasted and then like a good wing-man I began to scope out the crowd for Mary. We discussed the merits of different pick-up techniques and the differences between the les and the hetero approaches. We were both having a good time when all of a sudden I heard a scream of delight. Mary was hugging a woman and they were both jumping up and down.
The woman was tall about 5'10" and had long straight blonde hair in a ponytail. She was wearing a red riding jacket like English ladies wear hunting, and tight tan jodhpurs, those stretch riding pants. Mary and this woman hugged and squealed. When they final ended their embrace Mary introduced her friend.
"This is Emma. She is one of my oldest friends and I haven't scene her in at least 7 years. Emma, this is my good friend and art school chum, Dre."
We extended handshakes and hellos and Emma asked, "so hmmm, are you two a couple?"
"Heavens NO!" exclaimed Mary. "I'm not even interested in men, I've come out Em. Dre is just a good friend and my wing-man tonight."
I could see a little sparkle in Emma's eyes, as she took hold of both Mary's hands and put them against her chest and looking at Mary said, "well then we have a lot in common, and so much to talk about. Oh! But first I want to introduce you to Billy!"
I could see Mary sink a bit as she forced a grin. Emma moved back through the crowd and emerged with a figure also dressed in very tight jodhpurs as well. When they came closer it was difficult to tell the gender of the androgynous figure. Billy, was wearing a puffy white shirt with long sleeves much like you'd see on an 18th century gentleman but more feminine, his hair was long and blond and cut in kind of a layered mop. He had full lips that were shiny with pink lip-gloss, he had on perfectly applied eye makeup, and he wore a black leather choker that matched his black leather riding boots.
Mary grabbed him by the arm and pushed him forward and said, "This is my wing... um...um... boy, Billy. We have been best friends forever even though Billy is so much prettier than me and I get's me sooo mad!"
We all chuckled and as I shook Billy's hand I couldn't help but notice how soft it was. Billy was truly beautiful in a non-gender-specific way. Looking at him created the same kind of feelings I had when looking at a beautiful woman.
"What's with the riding out fits?" Questioned Mary.
Billy said, "We're fox hunters, get it? FOX HUNTERS...? Oh well anyway let's get a drink and find a couch."
We all laughed and after some searching we found a couch and chatted about Mary and Emma and how they had been friends in high school. We also chatted about their coming out and how their life experiences were so similar. Billy was also adding his experience to the story and I for the most part just listened.
After a bit, Billy put his hand on my knee and said, "And poor Dre has been completely left out! Sorry sweetie. Well girls let's get this sexy guy on the dance floor so I don't look like a total loser, and Dre doesn't die of boredom!"
We all headed toward the pulsing music coming from the dance floor. The scene was quiet erotic. On the edge of the floor two women were kissing in the most gentle yet sensual way, their scantily clad bodies glistening with sweat. All possible combinations of people were enjoying the throb of the base and the deft touch of the DJ.
At first we all danced together, but it was obvious that Mary and Emma were interested in each other. Soon they were dancing like a couple, Mary's hands on Em's hips and Em's arms around Mary's shoulders.
I couldn't help but notice Billy's body. He was a great dancer. His skin was alabaster and he had deep blue eyes set off by dramatic eyeliner and long black lashes. His tight riding pants showed off lean but fit thighs and a very tight round butt. Several times he brushed up against me either turning so his ass pressed into my crotch or he let a hand linger on my shoulder, waist or chest. I have to admit that Billy was sexy and there was no doubt he was teasing me.
After an hour of dancing I looked over at Em and Mary and they were kissing each other. Billy mimed a drinking motion and we made our way to the bar. By now the 5280 club was packed and there was just enough room for me to squeeze into the bar. Billy slipped his hand around my waist and pushed up against me so that we could both order drinks. He smelled good like woman's perfume and as I turned to ask him what he wanted I couldn't help but notice his fine features and full glossy lips. There was an awkward pause as we froze for a moment face to face. I quickly said,
"What would you like to drink? How about a Mojito?"
"You read my mind sailor." Billy said with a coy grin.
I didn't want to move as I was enjoying Billy's arm around my waist and he wasn't moving either. I could feel his warm body pressed against me and I liked it. He leaned over just an inch from my ear and said,
"It appears we've done a good job tonight. It looks like Emma and Mary are hitting it off. So we got them laid... now what about us?"
Just then our drinks arrived. I was in a bit of shock. I took a big gulp finishing half. Billy was hot, and attractive in a way I had never experienced, and I didn't know what to do. Until that moment I hadn't considered anything that happened that night as more than just innocent flirting. But now it was happening. Did I want this man?
Billy gave me a sexy grin and I could feel the bulge of his package press against my hip. I knocked back the rest of my drink and Billy took my hand and pulled me back to the dance floor. He was doing a kind of backward samba as he led me to the dance floor his eyes locked on mine.
He placed my hands on his hips and we began to sway to the music. The crowd pressed in on us and soon my legs were between his and we were pressing against each other. Billy's hands wandered over my chest and shoulders, often caressing the nape of my neck. I began to reciprocate amazed at how slender his waist.
Soon we were face to face and it happened, we kissed. It was soft yet firm, more insistent than a woman's kiss. Billy was skilled with his tongue and it snaked into my mouth. I pulled him against me and my hands instinctively went to his ass. I could feel him moan into my mouth as I took two handfuls of butt and squeezed. I could not believe how erotic kissing Billy was and how good his body felt.
We continued to kiss on the dance floor, swaying to the pulse of the music. I could now feel his stiffening cock against my already hard 7" erection. Our lips parted and we simply smiled as we swayed to the music our hips locked together our hands on each others hips.
Billy smiled at me and tilted his head to the side and flipped his long blond hair. He said, "Hey wanna take me home?"
I nodded and Billy led me by the hand off the dance floor. Walking behind Billy I was amazed by his combination of feminine and masculine. He was about 5'10" his hips swayed and his ass was full and round, he had wide shoulders long slender arms, yet when he turned slightly I could see his delicious looking package and the outline of what appeared to be a nice size cock in his too-tight riding jodhpurs.
Half way to the door two leather biker types looked at Billy and nodded appreciatively. Here I was in this gay club and I had unintentionally made a conquest, or had Billy? I was flattered and confused but most of all completely horny.
As we stepped out into the cool night air I could see Billy's erect nipples and his pale smooth chest. I wanted this boy. Fortunately the cab line was short and Billy didn't live too far away.
We made out on the elevator ride up to his apartment. He surprised me by pushing me against the wall in the elevator and grabbing my cock and balls and squeezed them through my jeans as he looked at me and smiled. He just looked into my eyes and tightened and relaxed his grip as he sucked on the middle finger of my hand. His message was unmistakable.
His place was modern and very nice. I had found out that he was only 25 but made a bundle as a stylist. He kissed me quickly on the mouth then pushed me onto the couch.
"Get us something to drink baby while I go freshen up and slip into something sexier."
I couldn't imagine what would make Billy sexier than he was but I was not going to argue. I found a bottle of champagne in the fridge and since it was domestic and I was in essence a virgin I thought, "why not?"
I poured two glasses and drained mine. I was suddenly nervous. Was I doing the right thing? Should I run? My head was racing but my cock was still hard. Before I could work through all the different scenarios Billy walked into the room from his bedroom.
He looked amazing. He was wearing a pair of gold lame bikini panties the cradled his cock and balls like a bon-bon. He had on thigh-high nylons and a pair of gold high heel women's sandals. And to top it all off he was wearing a string of pearls.
"I thought you'd like my girlie side. Besides I'm betting you are new to this and this might help. You like?" said Billy
He turned around and bent over slightly showing off his perfect ass and long smooth legs. Yes I did like. I refilled my glass and brought another over to Billy and we toasted,
"To first times."
We clinked our glasses and drank. I slipped my arm around his waist and pulled him against me. Billy put his hand in my hair and we kissed passionately. He broke the kiss and motioned me to follow to the bedroom, giving me a good show of his round pantie clad ass.
Billy said, "stand here," pointing to the foot of the bed.
He kissed my neck as he unbuttoned my shirt, then my pants and pulled them down on my hips. Billy then moaned and dropped to his knees in front of me. He rubbed my bulge through my boxers, he was slow and deliberate driving me completely crazy with lust. He then took my cock, still clad in my shorts, and stroked it through the fabric. Continuing the tease Billy slowly pulled down my boxers until my rock hard cock popped out to Billy's delight.
"Mmmmm baby you have a nice cock, very tasty." Said Billy between licks and strokes of my thick hard on. "I love the pre-cum and you are giving me a lot. Mmmmm baby you taste so good."
Billy was a great cocksucker. He pushed me back on the bed and I scooted back so he could climb on. His gold pantie ass was in the air as he rested on his elbows sucking me off. From this angle Billy could have been a man or a woman. I realized that what had me turned-on was the sharing of an erotic, sexual experience with another soul. My inhibition seemed to slip away with that realization.
Billy now had my cock wet with saliva and he was making nasty slurping and sucking sounds. At one point I could feel him push down on my rod, making it go into his throat. Just like a porn star he repeatedly plunged all the way down and pulled off showing off long strings of sticky spit like a prize.
I was in heaven but I knew if I didn't stop this blowjob I'd cum, and I wanted this to last. I softly took hold of Billy's chin gently guiding him off my cock. He now straddled my chest and I could see the distinct outline of his hard tool in his gold panties. I rubbed his cock through the silky material.
Billy said in a breathy voice, "mmmmm my lover wants some boy cock?"
I pulled the panties down to reveal an uncut 6" cock. I stroked the shaft revealing the tip of Billy's cock head. I loved playing with and feeling Billy uncut cock and I stroked it with delight. Billy slid up my chest until his member was just within reach of my mouth. I pulled his foreskin back and the pre-cum covered dome of his cock head appeared. I move the foreskin back and forth over Billy's swollen mushroom head, it glistened in the low candle-light of the bedroom.
Billy was moaning and I began to lick the tip of his cock. I ran my tongue between the foreskin and his cock head savoring the taste of pre-cum that had collected there. I began to stroke him more vigorously and take more of the shaft in my mouth. His cock was thick and was widest just behind the head. I loved the velvety texture of it on my tongue. I drooled as I suck his cock in and out of my mouth.
Billy was now moaning and encouraging me as I sucked. "Come on baby suck me good. Take my cock in that hot mouth and suck it good, Fuck, yes babe do me, oh fuck, oh fuck, mmmmmm yeah suck it you fine cocksucker."
Billy gasped and pushed me off his cock. He reached over to the nightstand to open the drawer. He had to slide further up in the process. I took advantage of the situation to grab two full hands of ass and suck on his clean-shaven balls. He moaned in approval. After giving his nut sack a thorough sucking I pulled his ass to my mouth and rimmed his hole. I thought to myself that I could get to like this.
Billy said in a halting voice, "you know what I need babe."
He spun around so we were in a 69 position, after giving my hard cock a few nasty sucks he slid a condom on my bone and covered it in lube. Balancing himself over my erection he positioned his ass to fuck me. We were now facing each other and his shaggy mop of hair was slightly wet from the sweat on his face. His dark eye makeup made him look just like Daryl Hannah in Blade Runner and he gasped as he pushed himself down on my cock. However unlike Daryl Hannah he had a beautiful stiff boner pointing out at a 45 degree angle.
The sight of Billy, my cock in his ass and his cock so hard and throbbing was amazing. He worked more of my member into to his tight hole. It felt so unbelievably good. I began to thrust back and Billy began to smile as he fucked me.
As our pace increased his hard cock swung up and down, hitting my pelvis on the down-thrust. I had my hands on his ass encouraging him to take my cock in long full strokes. Billy would occasionally reach down and stroke himself as we fucked in this position.
"Oh baby, oh baby, oh fuckin baby, I love your fat cock inside me. Fuck your boy bitch good baby, yeah mmmmm fuck my ass soooo fuckin good." Billy hissed over and over as he bounced on my rock-hard cock.
I was reaching the point of no return. Billy let out a gasp and his head went back and his mouth opened. He was stroking his cock and a long rope of cum shot out. It landed across my face and neck. He gasped again and his body shuttered and another rope of cum landed on my chest, neck and chin. Billy's cum continued to flow from his cock and covered his hand and ran down onto my body.
I said, "Billy I'm going to cum baby."
He quickly dismounted and pulled off my condom going down on my cock his legs on either side of my head. I quickly took his still firm boner into my mouth and tasted and sucked the last bit of cum out of Billy as I reached orgasm.
My back arched and a powerful wave erupted from my core. Billy squeezed the base of my cock hard as my orgasm exploded in a rush. Wave-after-wave, I was cumming and cumming as I moaned with Billy's cock in my mouth. Billy hummed in appreciation and delight as he pumped my cock mercilessly his mouth sucking hard on my cock head.
We both collapsed in a cum-covered 69. Billy lifted himself and lay on top of me. I could see his face covered in cum and he was smiling and holding something in his mouth. We kissed and he pushed a mouthful of sperm and saliva into me. I swallowed it down greedily as we swapped sticky tongues.
Billy lay on top of me. I could feel his cock against mine as I squeezed his ass. We kissed and laughed until we both started to get hard again.
Billy said, "Do you think Emma and Mary are having this much fun?"
I said, "who?"
We made love into the morning, it was amazing. Billy and I hook up often. My bisexual awakening has been a revelation and I feel I am growing as a person and a lover all thanks to beautiful Billy.