I waited a long time for this

I married in my middle twenties to a wonderful woman.  While the marriage was great, our bedroom activities were always a little off for me.  She was a straight missionary sex kind of girl while I wanted to explore a fantasy world of sexual delights.

When I would suggest fantasies, or porn to see what turned us on, she would half-heartedly agree, and I dropped the effort given her lack of enthusiasm for such things.

After twenty years of a great marriage, I went on a business trip far from home.  Rather than stay at the hotel, I searched for nearby nightclubs to see what they had to offer.  The flashiest advertisement was for a gay nightclub and they were featuring a drag show with lauded singing entertainment that night.  I laughed to myself and thought, “And now for something REALLY different.”

I got there a little early hoping to find a good seat to watch the show.  By all accounts, the venue featured quality entertainment and this show was a favorite in particular.  I spotted a table near the stage with only one person sitting there.  I asked him if he was saving the seats and he smiled saying he was alone and I was welcome to sit where I liked.  He added that he was sure the table would be full in another few minutes because the show was that good.

I ordered a beer and we made small talk as we waited.  He said that his wife refused to join him at a gay bar so he came alone.  I admitted that my wife wouldn’t have joined me either, but I lived a long way from there and I had no plans to tell her what I did on this trip.

The guy said his name was Paul and I shook his hand as I told him my name was Art.  The table did fill up quickly and the show began.  It really was impressive!  The singing and dancing were professional quality and they picked music that really appealed to the crowd.  I found myself not only entertained, but somewhat aroused seeing these sexy “ladies” hiding something extra underneath the sparkling dresses.

During the intermission, Paul and I discussed the show and our impressions of it.  He enjoyed it as well, and I was a little embarrassed when he admitted he was turned on by some of the singers.  I blushed and just nodded my head without saying anything aloud.  It was then that I saw Paul was clearly checking out my crotch for hints of how I was hung.  I found myself doing the same in reverse and saw he wasn’t kidding when he said the show turned him on.

He had an impressive erection reaching down his left leg and I could tell he was uncut by the way it showed through his pants.  He caught me looking but said nothing given that the second half of the show was about to start.

When the show was over, one of the singers walked over to the table and Paul stood to give “her” a hug.  I watched as she suggestively ground herself against him.  I was a bit in shock when he pulled back and said, “Lily, this is my friend Art.  He’s new and from out of town.” 

Lily moved over to give me a hug just like the one she gave Paul.  I could feel her manhood pressing against me.  No one was more surprised than me when my primal urges revealed themselves.  Within seconds I was hard as a rock and found my hands reaching to cup her perfect ass.

“Woah cowboy,” she said, but she wasn’t angry.  “They frown on PDAs around here when there’s a mixed crowd.”

Embarrassed, I withdrew having to expose my raging erection to anyone looking.  I peered over at Paul but his eyes did not meet mine.  He looked up from my beltline and addressed Lily.

“Art wants to join us after you’re ready to go,” he said with a wicked smile.

“That’s fine with me,” she laughed.  “The more the merrier we’ll be.”  And she turned to go back stage.

I was dumbfounded just staring at Paul.  He motioned to the chair and we sat down again.  I was too embarrassed to look at him and half-hoping, half-fearing what came next.

Paul broke the awkward silence.  “I’ve known Lily a while now.  We met here and on the nights I come to see her perform, we usually get together after the show.”

My erection had settled down by this time, but my mind still raced over all the implications of what had just happened.  I finally got the nerve to ask, “Were you serious about me joining you two?  If you were, what all will that entail?”

He laughed so loud he had to gather himself enough to answer.  “Look, I love my wife but I’m an SSA.  That’s same-sex-attracted.  My head is wired to want to have sex with guys but close relationships with women.  From what I’ve seen out of you tonight, we are the same.”

I was quiet as I considered what he had just said.  He wasn’t wrong.  I knew that gay sex didn’t scare me, but I’d never thought I was gay because I had no desire to date men.  However, what I had just discovered about myself was that I wanted to have sex with men more than I had any woman.

“Does your wife know?” I asked.

“No, and I’m not going to tell her,” he said without regret.  If I told her she’d assume I don’t want to be married to her and she’d be wrong.  But nothing with a woman satisfies me sexually as much as Lily does.  I’m hoping to branch out tonight if you’ll join us.”

Before I could say anything, Lily sat down next to Paul.  She smiled at him and then at me saying, “So where are we headed boys?”

Paul kept looking at me while he answered, “Art was just deciding that very question.”

I decided to throw caution to the wind and said, “Let’s go back to my hotel room.  It’s got a stocked wet bar, and we can decide what else we want to do from there.”

Art drove us to the hotel.  I had taken an Uber and Lily lived within walking distance to the club.  When we got to the room, I played bartender making the drinks.  Lily and Paul had no problem with PDA now, especially since I was the only “public” to see them.  I set the plastic glasses down on the round table and suggested a toast.  Each of us picked up our drink of choice.  I raised mine and said, “May this be a night to remember.  At least I’m sure I won’t forget it!”  We all laughed and sealed the toast with our upturned drinks.

I went to refill our cups and Lily opened her purse to pull out a small Bluetooth speaker.  She punched a few buttons on it and her phone and the music started to fill the room.  I was already feeling drunk so I missed the part where she started taking off her clothes.  When I looked up after setting down the next round of drinks I was amazed.

Lily was clearly male.  She had on a sexy Speedo-like pair of panties and a pink negligee that hardly covered the tightest ass I’d seen on anyone.  She was moving her hips to the beat of the music and positioned herself directly in front of Paul.  He slid down in his chair relaxing into the moment and waiting for the real show to begin.

I would describe Lily as pretty for a girl, and beautiful for a man.  Her whole body was shaved so clean that I guessed she had all the body hair lasered off at some point.  Even though she was well-hung, I could tell she had no balls.  I had read doing that lowered the amount of medical maintenance it took to keep her looking more female than male.  Her abs had great definition as did her arms and legs.  With most of her clothes off, she was as much male as she was female, except that her cock was growing.

Paul reached out and started to caress her penis.  Though she was uncut, the inner head cleared the foreskin making it so I couldn’t tell from the outline.  Paul pulled the Speedo panties down tucking the elastic band underneath her empty nutsack.  She stepped forward and he didn’t hesitate to take her into his mouth.  The look on Lily’s face changed from seductive to blissful.  It looked like Paul knew what he was doing and, as far as they knew, I might as well have not been in the room.

This went on for another minute before Lily said, “Baby, don’t get me off yet.  I haven‘t been properly introduced to your friend.”  She smiled at me and pulled her cock back from Paul’s mouth and hands.  She did a sexy little dance to my side of the table and asked, “Have you ever been with a guy before?”

I was embarrassed to admit that I had not.  I shook my head and explained, “I’m happily married, and I’ve jerked off to gay porn many times, but I’ve never been with a guy before.”

“Well then this is going to be a night to remember!” she laughed as she got right in front of me shaking her hips to the music playing.  I was mesmerized by the hard glistening cock that danced in front of me.  I barely noticed that Paul was getting naked.  I couldn’t look away from the gorgeous erection moving back and forth like she was trying to hypnotize me.

“Go ahead, baby,” Lily said, “do what you know you want to do!”

Suddenly, Paul was next to her almost pushing her out of the way.  His raging hard on was bouncing off hers at a perpendicular angle.  He surprised me when he said, “Let me be his first blow job.  I’ve never had a gay virgin before.”  Lily just laughed and took two dance steps back while Paul took her place.

I was surprised that I became even more excited having what was unmistakably a naked horny man in front of me.  While I didn’t object to Lily’s smooth body, Paul was a normal guy with pubic hair and my cock said that worked better for me.

I grabbed his erection with my right hand and began to slowly stroke him.  I was fascinated with the way the sliding foreskin exposed the head of his penis.  He was so well hung that I was able to get a second hand on him as I continued to stroke his manhood.  Paul just groaned and almost whispered, “I remember my first cock.  Art, you are definitely going to remember this, and so am I.”

I scrunched my hands together enough to put the head in my mouth.  I could taste the salty sweet precum oozing out of him and I savored swallowing it as I kept moving my lips down his shaft.  I kept going until I pulled my left had away to make room.  Paul’s moans and pelvis thrusts let me know I was doing fine despite my lack of experience.

I heard Lily say from the bed, “You’re going to make him cum baby!  He won’t be done for the night.  Go ahead and get him off.”

Paul put his hands around the back of my head and started thrusting his cock down my throat.  He did this so quickly I gagged.  After three or four thrusts my throat started to get used to it and my gag reflex subsided.  He was holding my head so tightly I could tell he wanted me to stay still while he skull fucked me.  I hardly moved as he jammed himself down my throat at a ferocious pace.  Seconds later he exploded across my tongue.  I felt like I had just crammed a delicious eclair in my mouth and the cream center burst forth filling the scant available space inside me.  I kept swallowing trying to keep up with the creamy torrent.  His essence spilled over and I could feel his juices running down my chin.  I had never been turned on more in my life.

Paul finally pulled away and fell backwards onto the bed next to Lily.  I started wiping my mouth and chin as I looked at the two exposed cocks resting against their stomachs.  I was far from done and decided I needed to be as naked as they were.  My clothes were on the floor in seconds.

I then stood up and took a step until I was in front of Lily.  Her legs were bent over the edge of the bad.  She eagerly spread them to allow me access to finish what I had almost started with her.  She was not as well hung as Paul, but I felt her cock growing as I slipped her into my mouth.  I yanked her panties off as I bobbed my head over her erection holding her member tightly with my lips.  I lubed my middle finger up with the saliva dripping down her shaft and found her anus.  It slipped in easily because of my spit.  I started timing my head bobbing with my finger thrusts.  Lily gasped an “Oh My God” and grabbed on to my hair as her hips pumped back at me as hard as I was going down on her.

I worked a second finger inside her as I continued to caress her shaft with my lips and tongue.  As she relaxed, I slowly slipped a third finger inside her bum.  I was so horny I was ready for anal.  I stopped long enough to ask, “Do you want to come before I fuck you?”

Lily managed to gasp, “Oh God, fuck me now.  I want to feel you inside me.  Fuck me like we’re going to make a baby.”

She didn’t need to ask me twice.  I stood up and was happy to see Paul offering us a pillow to put under her lower back.  That raised her man pussy to the right angle and I did started rubing the head of my cock around her perfect anus.  My fingers made it easy to enter her pushing my hard on past the point of no return.  Soon I was in her balls deep and thrusting in this beautiful man’s ass like I’d been doing it all my life.

I was far too excited and horny to last long, but Lily seemed to be just as excited and ready to cum as I was.  She said, “Fuck me you stud!  I love getting the cock.  Pile-drive me to heaven.  Don’t hold back.  I like it rough.”

I could feel the orgasm building and I increased my pace faster than I had ever fucked before.  Lily screamed in ecstasy and I felt her cum spraying both of us.  I let loose and felt her hole become even more slippery as my cum spilled out escaping around my cock.  I collapsed to my knees and started licking her cum off her stomach.  She squealed in delight saying, “You are a quick study gay boy!”

I laughed a bit embarrassed.  I said, “This really is my first time, but, like I said before, I watched a lot of gay porn.”

Paul asked me, “So what do you think so far?”

I was born to suck cock,” I admitted.  I’d always cum having straight sex, but the fucking fireworks went off for me tonight as I’d never known they could.”

We stayed on the bed for a while just listening to the music.  Lily finally restarted the conversation.  “Do you know if you’re a top, bottom, or versatile yet?”  Paul quickly explained the terms to me in case I wasn’t familiar with them.

Only then did it occur to me what she was asking.  I searched my fantasies for how I felt about being fucked by a man.  I got butterflies in my stomach just thinking about it.  When I admitted this Lily got up and went back to her purse.  She pulled out three dildos, each one progressively larger than the previous.

“Roll over virgin,” Lily laughed.  “Let me prepare you for the ride of your life.”

I started to roll which was made easier when Paul pushed on my ass and shoulder so that I quickly landed on my stomach.  I could feel Lily move between my legs as they hung over the edge of the bed.  She widened her stance to spread my legs apart.  Paul was already lubing my asshole when Lily grabbed the smallest dildo.  It was pointed on the end and was about 6 inches long.  The girth was maybe an inch and a half at the hilt, so I figured this wasn’t going to hurt.

It didn’t hurt.  In fact, it was small enough, and I was lubed up so well, that it only felt good as she slid it slowly into me.  She kept thrusting it in and out of me until I could barely feel it.  She removed it and slowly worked me with the next larger dildo.  This one’s diameter was a little smaller than a normal sized 6 inch cock. I jumped a little when she first put it in me, but I quickly adjusted to it.

Lily reached for the largest dildo and lubed it up before lining it up with my bulls eye.  She advised, “Try to push out with your pussy like you’re taking a shit.”  I hadn’t thought of this before, but it worked.  In no time I was taking a dildo that was the size of a decent hung guy and loving it.

Lily said, “I think you’re ready for the real thing.  This time I’ll go first.”  Paul looked disappointed but he really was too big for a virgin to fuck.

The next thing I knew, Lily’s cock was knocking at my anal door.  It felt different from the dildos in that it felt softer, but I could tell that was just the difference between a real cock and silicon.  She was as erect now as she was before.  Her shaft quickly shot past the point of no return and my virginity was gone the same instant.  She started slowly pumping her hips into me and I was loving it.  But then she stopped and told me to turn over.  She was going to fuck me missionary style.

I flipped over and slid the pillow under my ass as I got close to the foot of the bed.  I felt her enter me again and I was thankful she had been so gentle in preparing me for this moment.  I looked up into her eyes and she smiled as she looked into my soul.

“I can tell you’ve been waiting for this your whole life,” Lily purred.  She kept sliding her cock in and out of me never breaking eye contact.  We could tell how much we were each enjoying this and there was no fear or shame involved.  I was lost in the ecstasy of being fucked for the first time and knowing how good we each felt about it.

“I’m ready to go again,” Paul said breaking my reverie.

“Baby, are you ready for a real cock?” she asked.  I thought she was kidding.  Paul was really hung.  I answered, “I don’t think you brought big enough dildos to get me ready for him.”

The next thing I knew lily had moved and Paul, with his hard cock in hand, was lubing it up and ready to fuck me.  He had a wild look of lust in his eyes and I wondered if he was going to stop if I couldn’t take it.

“Baby, I’ll help you through this,” she purred.  “Remember to push out with your muscles when he enters you.  That minimizes the initial pain and you’ll be orgasming off this stud’s horse cock in no time.”

I jumped when I felt the head of Paul’s cock moving in.  I was thankful he didn’t just push it inside me as he had with the blow job.  What really turned me on was how horny I had made this guy.  He wanted me and he wasn’t to be denied.  I was surprised how much it turned me on to be lusted after by this man.  I could tell he wanted me as much or more than anyone in his whole life.  As he filled me with his manhood, I was close to screaming the pressure was so tight.  I remembered to push out and that helped a lot.  I could feel Paul or Lily adding more lube below and that helped too.  Eventually Lily squealed, “He’s all the way in honey!  Damned if you weren’t born for this!”

Paul began moving his hips and driving his shaft like a piston inside of me.  I began to naturally assume the female role in our coupling.  My joy in getting slammed like this was knowing how much pleasure I was bringing to this stallion riding me for all I was worth.  The facial expressions he made and the veins bulging from his neck must have knocked the testosterone out of me.  I felt like a sexy woman who wanted to please her man.  My greatest desire was to have him fill me with his essence.  I wanted his seed and I wrapped my arms and legs around him to coax him on to a big finish.

He reacted by slamming against me more than ever.  I doubt he could have fucked me any harder when his guttural grunts began.  His primal groans got louder as the orgasm in his loins raged forth.  I could tell I was close to cumming as well, but the tickle wasn’t centered around my cock.  It built up from inside of me and my orgasm flooded throughout my pelvis and stomach.  I was trying not to scream but I couldn’t help it.  I wanted this moment to last forever and I held onto Paul for all I was worth.

Paul lay next to me on the king-sized bed and Lily joined us on my other side.  I could tell they were reminiscing, but this was my moment.  The night was young and I had already decided to extend my business trip.  I’d figure out how this would fit into my marriage later.  For now, I had everything I needed.