The night with Greg and Tim ended up being a one-time thing. Greg simply stopped returning my calls and Tim never called again. In the three years that followed, I only connected with two guys in person as Jenni. Both meetings resulted in quickie blowjobs that took far more work and risk compared to the amount of satisfaction that followed. I recognized that I wasn't the hot piece of twenty-something ass I used to be, but the effort I made being Jenni could have, and should have produced better results.

Boredom with my job set in and I was lured back to the hospitality industry where I had started after college. While I was excited to pursue a new career path this time around, I also knew my opportunities to enjoy life as Jenni would diminish greatly. My wife accepted, but never really endorsed the lifestyle as something that she wanted to explore with me either. After a lengthy conversation very early in our marriage, she told me I was free to explore but made me promise never to bring anything home. I was at a point in my life where I simply refused to take risks that would push the envelope with my real-life situation.

Fast forward a little over a year. The new job was going great and the sex at home was incredible. My time surfing the internet and flirting in chat rooms increased, but being Jenni was an experience. An experience I missed terribly. After a year of employment, I had incentives kick in, including a healthy stipend for continuing education and travel. My employer was big into "career development" so when I presented them with a five-day industry conference in Las Vegas, there was no hesitation to let me register and book my trip.

I had a strong friendship with three fellow managers who all lived locally. Through a group of mutual friends, one of the guys in the group, John I had known for several years. The Las Vegas conference became a topic of conversation over drinks after work one night. Each of them used my attendance to convince their own establishments that this would be a great idea. My excitement about Vegas and a chance to explore Sin City as Jenni was disrupted at the prospect of five days with three tag-alongs. I flat-out rejected the idea of sharing a room or all of us staying in one large "party suite". I needed my Jenni time and was determined to get it at all costs.

In many ways, the preparation was just as exciting as the transformation. I could go years at a time not going online or shopping at a mall but when it was time to shop, I was ready to go. I had reached an age where the intimidation of walking through a women's clothing store was long gone. I didn't hesitate to hold up a dress or top against myself while checking it out in a mirror. Shopping for lingerie was even more enjoyable especially when I would get share with an overly helpful sales lady that it was for me. When I was done, it didn't surprise me that my five-day trip to Vegas was going to require two large suitcases and thick skin to absorb the ribs from my travel companions who were all carrying a single bag.

I felt the first night there should be for the boys. I figured a solid night in the casinos, dinner, and maybe a trip to a strip club should put at least two of the three out of commission for night two. I knew my friends would come charging hard out of the gate and it would take a day or two to regroup. I knew them all too well. One never made it out of bed and the other looked miserable all day until he caught the eye of another conference attendee who convinced him he needed to go out with her that night. My closest friend of the group was John. While he and I clearly were the two survivors from the previous night out, a hangover headache took him out of the picture. As we were discussing plans, I made up a story about a family friend who moved to Henderson a few years back. I would connect with him since everyone seems to need a recovery day. We both decided we'd take it easy and hit it hard again the next night.

I blew off the conference that afternoon to spend time relaxing and starting my transformation. After a nice lunch in the room, I started pampering myself and getting ready for my night out. I was sipping a glass of champagne as I took a scented bath, shaved, and did my makeup. It had been a while but when I stepped back and admired my work, I was quite pleased. A lengthy masturbation earlier in the afternoon helped keep any erection in check. I could easily tuck my cock and balls away as I put on black panties and pulled up a pair of fashionable tights up over them. I remembered how much I loved the tight fight of a bra against my chest as I slid my arms though the straps of the black lace push-up bra and connected the clasp in the back. I adjusted both of my breasts in the cups giving me a nice perky natural look. I had decided on a purple crushed velvet dress that would go great with a pair of black knee-high boots I had bought. I stepped into the dress and zipped it up my back. It fit perfectly. The boots absolutely made the outfit.

I went back the bathroom and attached a pair of clip-on hoop earrings and made a few adjustments to my makeup. I took a sip of champagne, stepped back, and admired myself in the mirror. I looked sexy and felt very confident. I considered a few adjustments to give myself a little more curve in my ass and hips but figured if I got lucky and the clothes came off, the less I had on underneath, the better off I'd be. The things forty-something Jenni thought about compared to my teens was mind-numbing. I had told myself I would leave around nine o'clock and realized that I had about thirty minutes to kill. I filled my purse with all the accessories I needed, topped off my glass of champagne, and sat down to relax.

I started to think about leaving my room and how I would make my way to the concierge. There was an older gentleman working at the stand who said he would take care of me with a cab and make sure I'd end up a very friendly club. My mind was wandering, thinking about the night, when I heard a key card inserted in my door. At first, I figured it was just someone at the wrong room. But when the door slowly began to push open, I quickly stood up in a panic. My first reaction was to run to the bathroom and hide there but there was no time as John pushed the door open and immediately made eye contact with me.

"Oh shit!" he said, startled that there was a female in the room. "I am so sorry. I don't know what happened, I thought this was my friend's room."

I had the perfect out, but instead of playing it off as the wrong room, for some reason, I decided to come clean. John was a free spirit. The type who was proud that he woke up with "morning wood" every day and the fact that he masturbated daily. So proud, it wasn't uncommon for him to want to share details of his personal sex life including his own private moments, sex with his wife, and his adventures outside of his marriage as well. John was horny all the time. If anyone would understand, it would be him.

"John, you're in the right room. Come in and close the door," I said in my natural voice versus my softer more feminine tone I would have used as Jenni.

"Holy fuck! Fuck me, I knew it!"

"What did you know?"

The door closed behind him, he dropped his bag and walked toward me. His eyes looked me over from top to bottom.

"I knew there was something up with you. Very coy about your plans. The way you were sneaking around and shit, I thought for sure you had a girl in here with you or something. Fuck dude, look at you. YOU are the girl you were hiding!"

"Well, judging from the look on your face, you're impressed, aren't you?"

"Impressed? Fuck dude, I'm fucking horny as fuck. No way! You’re a chick!"

"Can you stop calling me dude and chick?" I paused. “My name is Jenni,” I said in a more feminine voice.

"Oh my god! If you have a name and everything that means this is not the first time you’ve done this? And fuck look at all this,” he said motioning to my clothing items that were laying around the room. “This is so fucking hot!"

I took a deep breath, filled my glass, and offered a drink to John who quickly accepted.

"So, I would rather this doesn't get circulated around the group. I've worked very hard to keep Jenni separated from the rest of my life. Especially my home life. I'd like it to keep it that way. Cool?" I asked.

"No problem. But seriously, can I ask you a few questions? Like, does your wife know? Wait, how long have you been doing this? Holy shit, I have a million questions. But du.... Jenni, seriously, smoking hot. I’m impressed,” John said as he sat back on the couch and took a long sip from his drink.

"Well, thank you. I was planning to head out to a bar soon, but I guess we can play twenty questions, or a million questions, first," I said as I sat back down. "I'm down for anything you want to ask. But, to answer your first two questions, my wife kind of found out I did this at one point, but it is not something that EVER comes up, and she likely has no idea."

John motioned that he was zipping his lips closed.

“And I started when I was sixteen years old.”

"Are you gay?" was the next question he blurted out. I shook my head in disapproval.

"Have I sucked a dick? Yes. Have I been fucked before? Yes. Have I loved a man before? Yes, probably. I am also married and have a family. Am I gay? You tell me."

"I suppose you are kind of bisexual or something then, huh? Bro, you’ve sucked a dick before. Did you like it? Wait, sixteen? Holy shit.”

My frustration with John’s sophomoric line of questions was clearly visible and he immediately apologized. To be fair, and to try and embarrass him at the same time, I answered his question.

“I love sucking cock. I love pleasing a man with my mouth. And I really love the taste of cum! You should really try it sometime. You, more than anyone I know, would love it. And yes, sixteen. It’s a remarkable story. Next question.”

John started to blush which was no easy task to accomplish. We went back and forth for a while with questions and answers. I found myself interested in my own story and I was as amazed with my experiences as much as John.

"This is all very overwhelming. Cool, but holy shit. VERY overwhelming. So, you were just heading out tonight?” John asked. “You could have walked by our group and none of us would have known it was you." John said shaking his head in disbelief.

"Yeah. You would have checked me out and thought about how you'd love that piece of ass as I walked by as well. Think about that," I offered as a thought. "And by the way, John, my questions for you are why are you even here and how did you get a room key?" I asked him.

"Oh yeah, I took one of your key cards last night. Karl was bringing a girl back to his room and Eric wanted to crash in mine. So, I figured I'd hang here and wait for you to get back from your friend's place. Honestly, I knew you had a suite and probably a more relaxing place to hang out once I got done gambling."

"All good. So, do you want to out with me or not?” I asked. “Let's get some drinks or something. Why don't you get dressed and let's go out," I said in a very bratty 'I want my way' kind of tone.

"We have all night for me to tell you stories. Just a few hours and then we'll come back.”

John agreed. He ran back to his room for a change of clothes and met me at the front of the hotel in less than thirty minutes. I spent most of the taxi ride telling him my history. He sat quietly and took in every detail I was giving him. It wasn't often John was speechless, but I managed to pull it off. The club was a blast. The crowd was very diverse, and we had fun people-watching. John was particularly enthralled by how easily I flirted with both men and women. It was a vast difference to my more reserved demeanor he was familiar with. When I shared a kiss with a guy who had been flirting with me all night, John lost his shit. He looked jealous and turned on at the same time.

Before we realized it, we had both had more than a few drinks and it was after midnight. We both decided it was time to head back to the hotel. I knew the look John was giving me and that I’d have a decision to make when we got back. I spent the first half of the taxi ride touching up my makeup. John watched intently as I did. The second half of the ride was small talk about the night and what our plans were going to be when we got back to the hotel.

I invited John to stay in my room but insisted that nothing was going to happen between the two of us. We had been friends for too long and a night like this one could ruin that friendship. I think we both knew otherwise.

"I totally agree," he said with truly little conviction. "If I have to share a bed with someone tonight, I would much rather it be you than Eric. Nothing will happen."

The more he talked, the less convinced I became. I knew as we rode up the elevator and walked down the long hallway to the room that there was no way that "nothing" was going to happen.

As soon as the door closed behind us, John right hand found my ass and I turned to face him. Our lips connected.

John was a great kisser. The connection between our lips and tongues was very natural. It was the kind of kiss that could have lasted all night. His hands rubbed down my back and squeezed my ass. One of my hands went to the back of his neck the other to his ass. Never in my wildest thoughts did I imagine being in this position, with John of all people. There was never a time that I thought about John in this way, but when he whispered in my ear, I knew tonight was different.

"Oh my god, I'm so fucking hard right now."

I could feel him growing as we were standing and kissing but I was avoiding the temptation. I looked between his legs and saw his cock straining underneath his pants. I stopped, took John by the hand, and walked to the bed. We both sat on the edge and looked him in the eye. John and I had known one another for over a decade.

"If we do this, there can't be any regrets. Whatever happens, happens. It stays in this room. Tomorrow is tomorrow."

He leaned over and kissed me. Assuming that was his way of answering that he agreed, I gave in to my desire and allowed my hand to slide to this cock. I slowly started to rub it over his pants. As the kissing became very intense, John's exploration of my body became more aggressive. His hands began cupping my bra, rubbing down my side and feeling my smooth legs. I stood up and faced him as he was on the bed looking up at me. I locked my eyes on his as I reached down to unfasten his belt, undid his pants, and slid them down his legs. His cock was huge. It stretched his athletic briefs and longed to be released. I had seen John flaccid before in the gym locker room and always figured he would be big. He didn't disappoint me with his size.

I pulled his shorts down allowing his massive cock to spring free. His cock was at least nine inches and had a nice thick girth to it. The head was perfectly shaped. There was no stopping at that point. We were well past writing this off as getting caught, having a little fun, or hanging out at a club. With his cock in my hands, I knelt in front of him and started to suck his monster. I looked over and saw myself in the mirror. Never in my wildest dreams did I ever imagine getting caught by a friend would produce this result. I was sucking the cock of one of my best friends and loving it.

My mouth, lips, and tongue worked over every inch of his cock and balls. I started to taste him after about ten minutes and minutes later the biggest shot of cum I’d ever experienced hit the back of my throat. And then another. And another. As wave after wave of his cum filled my mouth, John moved his hands to the back of my head forcefully holding his cock in my mouth. He yelled at me to swallow in a very assertive fashion while he started fucking my mouth, slamming his cock and hips into my face as he did.

"Enough of Mr. Nice Guy, this is your punishment for holding out on me all these years," he started as he continued to fuck my mouth. His cock was as rock hard as ever and still pumping cum down my throat.

"This is just the start. Think about when I would tell you my house was empty or my family was traveling, you didn't think I would have fucked you. All those times I would tell you how horny I was, you could have come and sucked my cock. Fuck you! Well, we're just getting started tonight."

After swapping positions and throwing me down on the bed, John started removing my tights and panties. When he realized my boots were still on, he quickly removed them from my legs. His hand slid up and down my freshly shaven legs. I noticed his cock was still hard and grabbed it with my hand. John pulled me to the edge of the bed and put his cock up against my tight bud. I knew this was going to hurt. He spit down on my tight hole a few times and then on his cock before sliding the head inside me. Even he realized this may take a moment as he slowly eased his cock inside me. My hands dug into his hips as I started to tear up.

"You like that don't you? You like my cock slowly filling you up. I want to stretch you so bad. Fuck!"

I moaned in agony and delight.

I’ve never experienced so much pleasure and pain as I did for the first three or four minutes of him inside of me. He slowly inserted himself and it wasn’t long before I willingly accepted his entire cock inside me. The entire situation was overwhelming. I could feel him pushing his cock deep inside of me. After holding it there for a moment, he slowly started to withdraw before pushing it back inside me. It wasn't long before we had a wonderful rhythm with his hips thrusting against me and his cock sliding in and out of me. He would slow down at times just when I thought he was getting ready to cum. Other times he would thrust his cock so deep inside that I felt nauseous. He was gentle at times and rough at others. I was not surprised that John was incredibly good at sex. His pace quickened as he started to swell inside me. I knew he was getting ready to cum again.

"Cum inside me you fucker," I demanded.

"I'm not pulling out! I want all of me inside you. I want you to think about my cum inside you tomorrow you little slut!"

"Yes, baby! Harder, harder," I screamed.

John ravaged my ass with his cock pounding it harder and deeper inside of me with every thrust. With one last thrust, both of us passionately screaming at each other, I felt his cum shoot into me, stream after stream. While his cock continued to produce an endless supply of cum, he leaned down and told me to kiss him. I obliged. His cock inside, my lips against his, our sweat and sex-covered bodies collapse into each other.

Other than each of us trying to catch our breath, the room was silent. John and I crawled toward the pillows. His cock had slid out while we moved but my instinct was to find it and hold it as we lay there in bed. I loved how it felt, especially covered in his own cum. I started stroking it softly.

“Go and suck it again,” John demanded. “I’m not here to cuddle. I want to fuck.”

Without objection, I slid back down toward the foot of the bed and took his cock in my mouth. I could taste him as I swirled my tongue around his dick. I stroked it with one hand as I circled his head multiple times before licking down the shaft to his balls. I took them both in my mouth and sucked on his sac before licking back to the top. I took his cock back in my mouth and started to feel him respond.

“Fucking A! Where did you learn to suck a dick? You are an incredible cock sucker, aren’t you?” he asked.

“I told you; I love sucking cock! What can I say?” I responded as I came up for air.

My lips immediately reattached to his balls, giving them an extra tight squeeze in my mouth as I sucked them. Hearing John moan his approval turned me on. My tongue licked back to his head and then I took his cock deep in my throat. I knew John was watching me and really into the moment. I knew he and his wife had incredibly outrageous sex. John wasn’t shy about telling us all about it.

But in the moment, he was all about me sucking his dick. I loved it. It didn't take long for John to want to fuck me again. He rolled me over and mounted me from behind. He was far less forgiving this time around. The head of his dick quickly penetrated me, and his cock filled me on the first thrust.

I wasn't sure what John would have left in him for sex. Between the amount of alcohol we consumed, and the sex we had already engaged in, I was expected much less than what I got. Feeling John repeatedly thrusting his cock inside me was rocking my world. I was completely oblivious to the fact that my own dick had been rock hard until I felt a pool of cum forming on the bed under my belly. It wasn't long after that I felt John’s cock swelling inside me before unloading another load of cum inside me. We both collapsed to the bed, exhausted.

I woke up a few hours later and realized we had both passed out. I looked at John naked beside me. I slid out of bed and figured I'd clean up a bit before going to sleep. I looked at myself in the mirror. I was a mess. After a long shower, I slid on a pair of shorts and a tee shirt and decided the pull-out couch might be a better place to sleep. There would be no hiding what happened. My makeup, clothes, shoes, and all my accessories were scattered about the room. I would leave them there to stimulate conversation when we both woke up. I stared at the ceiling forever before finally falling asleep, wondering what the next day would bring.