Drag Queen and the Indecisive Guy

Walking down the steps my mind was at war with itself. My two personalities were screaming at each other. I have always had debates in my head. I envy those who know what they want or know what must be done without hesitation. I was never that lucky. Every decision was a WWE match between my ears. Indecision was my middle name. Mostly the internal argument was between what part of me said was the right and proper thing to do and what I wanted to do. It was like having my Irish catholic grandmother in one ear and a drunken frat brother in the other.

I always thought of myself as mostly invisible. I wasn't fat, but I certainly wasn't in shape. I wasn't hard to look at, but I didn't stand out in a crowd either. My raging inferiority complex usually left me in the back of the room, at the end of the bar or on the edge of any social activity. The only thing that made me even remotely different was I was gay -- in denial -- but definitely gay. I didn't think of myself as gay in those days. It was just a phase I told myself. Since I didn't do well with women, I was having gay sex to get by until SHE came along. The list of rationalizations was extensive, and all carefully crafted to shield myself from a simple fact -- I was gay.

All my gay sex had happened in glory holes mostly. I experimented as a teen, like so many do. When I got into my early 20s I discovered video booths with holes in the walls. Fingers appeared in the dark, my cock went through the hole and a warm wet mouth consumed it. I came and left. Simple, uncomplicated and unfulfilling. I sucked my first cock when the guy in the booth next to me sucked me for a second then he pulled off. I saw the light in his booth as he left and then a quiet knock on my door. I let him in. Rather than sinking to his knees he gently pressed me to my knees. He undid his zipper and there was a big, hard cock in front of me. I froze but his hands urged me forward. I was both afraid of denying him, he was mature and strong and looked serious, and I wanted to take it in. I opened my mouth and he slowly took my face. In a few minutes I tasted a flood in my mouth. He pulled out, I spit his cum on the floor and fled. I was nauseated at what I had done. But that nausea quickly turned to fantasy for me.

Having had a sample of what it's like to please a man to orgasm I began to go back to the booths to suck rather than be sucked. I became brave and went into booths with other men. I liked the feeling of their hands on my head. Late one night I was kneeling and sucking when his hands lifted me, looked me in the eye and kissed me. My first gay kiss.

"Will you come home with me?" he asked

"yes" was all I could muster.

I don't know why I said yes but in retrospect it was bound to happen eventually.

I followed him to his apartment. He took me to his bed and for the first time I laid with a man. He was gentle, kind and passionate. He made love to me rather than just raw sex. And he took my cherry. I had fantasized about it but he made it happen. He made me cum as he came inside me. As soon I realized what happened I got up and fled. I didn't get a phone number, so I never could call him to apologize. But that night was a life changing event for me. But I rebuilt my rationalizations and for the next couple of years I kept my gay events to a minimum and anonymous.

Those rationalizations were being heavily tested at that moment. The steps I was descending went to the best-known gay bar in town. Pegasus was the so well known that it was a punch line of a fag joke.
"What the fuck do you know -- you go to Pegasus" would always draw a laugh.

It was Halloween. I was drunk. A few friends and I had hit a bar or two on the night. I had not dressed. I am terrible with costumes. I simply lacked the imagination to come up with something I was comfortable with, not that my insecurity limited my options

On this Halloween night after the guys headed home, I headed back to my car. I passed under the Pegasus sign -- and heard the thumping loud music, paused, then walked by. I turned around and walked past again, slowly and then went past one more time. No -- just go home I thought. I was almost back to my car when I turned for the final time and stood at the top of the steps. Descending the steps to Pegasus was what happens when rationalizations fold under the weight of alcohol. Uncertain and terrified of being discovered I still wanted to go in. I needed to go in. I really wanted a man like that one I was with on that magnificent night. I screwed up my courage, opened the door and entered.

I paid a cover charge and walked into the bar. The music was pounding. Disco loud and proud. It was dark and hard to see. I had never been in a gay bar before and I didn't have a clue what I was doing. It was packed. To my delight it was packed with men in drag. It seems Halloween in the crossdressers national holiday. Most of them were over the top drag queens. A few were serious crossdressers and one or two might have been real women.

I squeezed into a place at the bar and waited for a bar tender. I looked around and saw men look me over. Up and down and then just look away, a reaction I was used to from women but a bit disappointing here. Once I got my drink, I did what I always do when I am uncomfortable, I wandered to the end of the bar and just hung but I did have a good view of the dance floor. The only real source of light in the room the dance floor was lit with colored spots and a couple of disco balls and it was mobbed. So many tall drag queens and men in leather. Like watching the ocean, it was always moving but never really changing.

As tunes ended some walked off the floor and others dived in. During one such change I saw a guy in over the top 70's drag. Tall, with killer legs in platform heels, black fish net stockings, a short skirt and a loose silk top with lots of lace. Heavy makeup under a wild blond afro style wig and rainbow hat. He was impossible to miss. He looked at me and I turned my eyes away. I didn't know gay protocols and didn't know how to handle it so I just hid best I could. He went to the bar but a few minutes later, as I was looking at the dance floor he appeared in front of me -- right in front of me. Looking right at me and smiling.

"Brandon" he shouted at me.

"Jim" I replied.

He leaned in for a quick kiss on my cheek and I am sure I blushed. We tried to chat, but it was like trying to have a conversation in a steel mill during a disco show -- impossible. He took my hand and found a corner where we might be heard. We proceeded on some awkward conversation, but I did tell him he looked really sexy. He smiled and twirled for me and put on his best coquettish smile. After about 20 minutes of shouting at each other he took my hand and headed to the door. Like some small child with naïve faith I went with him. We got outside, and he said:

"That's so much better. Would you like to come home with me?"

I was totally taken aback by the abruptness of the offer. In better light he was a good-looking guy. Killer blue eyes, handsome face or as best as I could tell under all that makeup. Tall and well built.

"Sure" I stammered in reply.

I had had been with men before, in video booths, glory holes really. Short, sordid encounters without words. At first, they wanted to suck me. I was thrilled with the idea and the pleasure. One evening a man who I expected to get on his knees instead pushed me to my knees. I took his cock in my mouth and in a few moments, he came, without warning. I tasted his cum and tried to pull off but he held my head in place and shoved his cock deep. I swallowed reflexively. He zipped up and left. I fled and was nauseated at the thought of what had just happened. As the weeks went by the memory became what I masturbated to. One night I met a guy at the glory holes who offered to take me back to his place, and I went. That was the first time I had real sex with a man. Kissing, foreplay and anal, me on top. I never knew his name but that night was a gateway event.

I was walking down the sidewalk with a drag queen -- hand in hand. Clearly my rationalizations were crumbling fast now. So much for being inconspicuous. It was only two blocks to the parking garage. Brandon had ridden down with a friend, so I drove him back. It wasn't far, cross a river, under an overpass and down a few streets. I followed him up his steps to his door. Nervous was an understatement, I could hear my heart pumping in my ears. This is only the second time I had gone home with a guy and frankly this guy was hot. Once inside and he turned and kissed me, like tongue in my mouth hot wet passionate kiss. I was not prepared for that. I thought we would have some chat time or he would tell me thanks for the ride. But his kiss was electric. My hands wandered all over his body like a starving blind man looking for lunch.

About two minutes into this intense make out session he pulled back and looked at me.

"I know you like the outfit, but I don't want to have sex like this. Can we go upstairs so I can change?"

"Sure" I stammered. Always the witty conversationalist.

He went into the bathroom and took a quick shower. While he did that, I tried to find a way to get comfortable. Should I undress? Just maybe to my pants? Underwear? Sit on the bed, lay down? As I said even the simplest decisions are made by committee in my head. While I was seeking a final decision on my socks he came back.

My jaw dropped. Brandon was stunning. A blond haired, blue eyed god. He was broad shouldered, thin waisted, fair skinned and wearing only a towel. He sat down next to me, let the towel drop and laid back. I was frozen. He was so beautiful, and so hot -- and so fucking well hung. He terrified me. I didn't want to get undressed. He would see how average I was and throw me out. But he didn't. He pulled me down on top of him and kissed me softly, sweetly, passionately and very, very thoroughly.

That kiss tore down my last inhibitions. I ignored the committee and got naked as fast as I could. I rolled into his arms and looked down at him and then began kissing. I had never really kissed a man like that. The kind of kissing that is totally committed, intimate and intense. He paused, looked up at me he put a hand to my face, looked me in the eye and told me:

"You are a handsome, a hot guy".

In all my life I had never heard that. Ever. Not handsome and certainly not hot. Looking back I started to fall for Brandon at that moment. He just touched me like nobody ever had. He made me feel good about myself. Now I really wanted him.

"Thank you -- I am not used to hearing that" I said in reply.

"It's true -- you are really handsome. I love dark haired, dark eyed men and you are so good looking. I thought maybe I wasn't what you were after, but I thought I would try."

"Brandon- you are simply the hottest man I have ever been with. You should be a model. If this is a drunken dream -- don't wake me. I really like this one" I smiled down at him.

The kissing intensified, and his hands were sliding down my back to my ass. Moving his hands down my body felt incredible. His warm, naked flesh was so sensual, so thrilling and his erection, pinned between us made me aware of every move of his body. I moved to kiss his neck, then down to his nipples. He giggled.

"Ticklish nipples -- sorry" he said.

"I will keep that in mind" as I licked his left nipple to see him squirm.

A beautiful valley ran between his two pecs to his stomach. He didn't have a six pack but it wasn't far from it. I just let myself slide down his body. His warm cock was now under my chin. Sitting up I took it in my hand -- and it was magnificent. Long, perfectly proportioned. I think he might have been a dildo model it was that perfect. I slid further down until I was below his cock and I rubbed my face all over his cock and balls, drinking in his aroma. I looked up and our eyes met. He had lust in his eyes. Brandon wanted me to go down on him and I was more than happy to oblige. This was sex like I had never known.

I licked up his shaft and swirled my tongue around his cock head. Opening my mouth, I started to take him in as I watched his face. I went as far down as I could, then a little bit further. Pulling back up I inhaled and did it again. I remembered that if you are going to deep throat a cock you need to relax your throat muscles. I tried. I really did. But I couldn't get him down my throat. After a few minutes he got up, flipped me over and pulled me to the edge of the bed until my head was half way over the end.

He stood and put his cock in my mouth. My eyes were looking directly at his balls and he started to slide into me.

"Relax Jim. Just relax and I will take care of the rest" he said in a very throaty voice.

I did my best. He began to press in and I watched his balls getting closer to my eyes. Hitting bottom, I concentrated on relaxing my throat and moved my head side to side slightly. Then I felt his cock slip into my throat. I didn't gag, and I was so proud. To make it all the better his warm soft balls now rested on my face and eyes. I was ecstatic. Brandon pumped very lightly inside my throat careful to not pull out too far. I put my hands on his ass cheeks and tried to pull him in deeper till my nose was pressed into his groin and I had taken every inch of that beautiful cock. Then I began to run out of air. He pulled out, a thread of my saliva connected to his glistening cock ran from my mouth, to my nose to his cock. For some reason that image has never left me.

A few seconds later he slid in again and again into my throat. As he was fucking my throat he bent forward and took my cock in his mouth. I didn't expect it and I moaned around his cock at the sensation of his warm mouth. I wanted to stay like that for as long as possible. I had never felt so alive, so sexually charged. With no idea how long, we stayed there he finally pulled out and laid down. I knelt on the bed and looked at him. I don't know how I got this lucky but that image of Brandon laying on his back in front of me will always be a warm spot in my memory.

I should have laid down beside him and make out some more but I didn't it. I slide up and put my knee over his hips and straddled him. I wanted him to fuck me. I wasn't an anal virgin but I wasn't exactly experienced either. It was a fevered impulse. I wasn't thinking I was reacting to what my body told me. And I ached to have him in me. My prior anal experience was a bit forced, on me. A faceless guy in a video booth lifted me up, pushed my jeans down and penetrated me. Damn that hurt at first. But the pain went away, and I just let him fuck me. He dumped a load in me, pulled up and took off. I felt his cum running down my leg and I felt humiliated. I don't think of it as rape since I was sucking his rather small cock, but it wasn't my choice either.

Stradling Brandon's stunning body I looked down at his face. I fumbled with his cock trying to get it into me. For the first time in my life I wanted sex with somebody on something other than a physical level. I I really liked Brandon. I wanted to please him. I wanted to know he found me sexy and desirable. I wanted to fuck for him as if somehow that confirmed his words. I actually felt an aching in my ass.

"Is that what you want" he huskily whispered to me.

I looked down and him and nodded.

The voices in my head had quieted leaving only a hunger to feel Brandon inside me. I had never been so completely consumed by a sexual urge in my life. It was almost animalistic. I wanted him, needed him.

He flipped me over onto my back. He slowly bent over me, my legs spreading wide for him and he kissed me deeply and passionately. I felt his cock on mine. We ground into each other as we kissed.

I squirmed beneath him. I was trying to position his cock at my hole and pushing into him. This was a fever the like of which I had never known. I lay on my back and looked up at him, his pretty face, his amazing body and then saw my legs around him. It was an erotic jolt. Too see myself so exposed, so eager to be taken my legs wide and inviting -- it was so sensual and fulfilling. It felt right, as if it was where I was supposed to be.

He reached over to the drawer in his nightstand. He brought out a bottle of lube and a condom. I watched patiently, eagerly, as he put he condom on and put a generous dollop of lube on his fingers.

"Relax and I will get you ready" he said.

He was gentle, sweet and thoughtful about what I needed. It was getting seriously emotional now. All my gay sex had been anonymous, faceless really except that one night. Brandon was making love to me, not just having sex with me. And I was falling fast and didn't even know it. At that moment I just surrender to the sensations. I trusted Brandon, and I had known him for maybe two hours. It should have set off alarms in my head, but I was way to lost in lust to notice.

The lube was cold and very slippery on my opening. He put a finger in me, I jumped but he went slowly. He took my cock in his mouth and my entire being was distilled down to the thrilling sensations. It was good I was drunk, or I would have cum right then and there. He moved his finger in and out, and with each stroke my pleasure meter dial went up a few more notches. Then he put two fingers in and my hips began to move into his hand. I caught his eye he smiled at me. I wanted every bit of Brandon I could get at that moment. I was so ready to have him in me.

He pulled out, slide up between my knees, and put some lube on his magnificent cock. I remember how it glistened with the lube and condom on it.

He put my legs on his shoulders, got above me and looked into my eyes. I felt his cock there, and he just froze. I whimpered I wanted him so badly. I began to press into his cock but I couldn't get it aligned right. I was like an animal in heat.

"This may hurt a bit but in a few seconds, you will be fine" he said.

I looked into his eyes and just wanted to melt. This gorgeous guy was about to enter me and I had never wanted anything more in my life.

His cock found my opening. I tried to relax. I felt the pressure and then the pain. His cock was a lot bigger than two fingers. I bit my lip but my fingers urged him on. He paused. My face was like an indicator for him. I relaxed, he pushed in a bit further, and again a wash of pain. After a few second he pushed again and I felt him pop in. The pain began to recede and my entire body relaxed. I put my arms around his neck and pulled him down to kiss me. He let my legs go and I just wrapped them around him.

"Fuck me Brandon" I whispered.

He began to move, slow deep strokes. I watched his face. His eyes would close as he enjoyed me, the sensation my eager ass was giving him. When he opened his eyes, I felt a surge of lust for him.

"Cum on me -- please? Don't leave it in the condom" I asked, pleaded really.

"On your face?" Brandon asked

Again I nodded. I wanted what was him on me. I didn't care where he came but I knew I wanted to please him, fulfill his urges with me. I wanted the reward to knowing how I satisfied him.

His temp increased, and I felt him deeper inside me. A few strokes made me squeal, it hurt a bit, but I loved it. I felt his hand on my cock and he began to stroke me.

"I am going to cum if you keep that up" I whimpered.

Brandon smiled down at me and kept pumping my cock. Then the stars came out. I came so hard it hit my face, over my head and left a pearly rope down my chest. I convulsed, my whole body just shuddered. He pumped into me a few more times, pulled out, tore off the condom and kneeled over my face. I licked his balls and in just a few seconds I felt his balls tighten up. I pushed my face in front of his cock. Just inches from my eyes I saw the jet appear. A stream of warm, slick cum hit my eyes, then my forehead and then my cheek. It felt like he came for days.