My Night Out

I have done this awful cycle every year since getting married. And every year I believed myself less and less. Every Halloween, I promised myself that I would indulge myself in my biggest fantasy, dressing like a woman and going out. But every year, I either had no chance or just chickened out. I have been a bit of a closet cross dresser throughout my marriage. Over the years I have played with various states of dress up, from lingerie to full on dress. Even now, the thought of donning a pair of panties and bra with some hose to match makes my breath catch in my chest. But as a married man, I have, for the most part, denied myself that pleasure. My wife is very strait laced and would look down on me if she ever knew I had such "perverted" tastes. So, I have buried this side of me. Since our third child she has lost all interest in sex. I have been in essentially a sexless marriage for the last 10 years. Making my spending time with myself all but inevitable.

So, it was with only a halfhearted effort that I thought about dressing this year. For one thing, I had nowhere to go. We had no party to go to and I had no interest in going to a bar on Halloween. For another thing, I have been very good about denying myself any cross-dressing extracurricular activities. I didn't want to get caught, and there are few chances to be alone in a house with 3 kids. But then opportunity came knocking.

I should take a little time to describe myself. I am not what you might consider "feminine". I am 5 foot 8, 175 pounds. But I am a very trim 175. I have been working out since I was 19 and I am only around 10% body fat. I have very shapely legs and a flat stomach. I am broad across the chest and decent sized guns. Just for kicks, I take most of the hair off my body, including shaving my legs, (which my wife thinks is weird) and my chest and armpits (which she thinks is fine). I have a youngish looking face which I keep clean shaven with short black hair.

So it was with shock that I found out my wife was planning to get out of town with my daughter over Halloween. They have been touring colleges and had a chance to go visit some schools over the holiday weekend. And as long as I had to work over that time, she was going to take the boys as well. So, for once I was going to be on my own.

I decided to take advantage of the situation and after the Halloween "trick or Treat hours ended at 7, I started to get dressed. I started off by taking a long shower and completely removing all remaining hair on my body and making sure my face was silky smooth. This was farther than I had ever gone before but I figured enough was enough. This was my one chance to really give things a go. Next, I dried off and applied lotion to my body. I needed to consciously not spend too much time on my genitals since I was quite aroused by all the attention I was giving myself. Next I put on a black waist cincher that my wife has to give myself an hourglass shape. I loved the feel of it on my body. It made me feel sexy and I started to feel very "transformed". I next donned a pair of black high cut boy shorts and a matching red and black bra stuffed with some gel inserts. Looking in the full length mirror, I started to lose it. I just wanted to lay down and jerk off right there. But I got my breathing under control. I had all night to get dressed and enjoy the feeling and I wanted to go for broke. I put on a pair of black thigh high stockings that I had bought on clearance and hid away for myself and then put on the three inch black strappy pumps in my (woman's) size eleven. I had picked these up over the summer at a garage sale. They were in great shape. I didn't even care about the strange look I got from the people having the sale. They fit perfectly and made my calves just pop. Next, I grabbed a black slip dress of my wife's. She is a size large, and I was hoping it would fit me. It was a little difficult getting on my chest, but it looked good once it was on. I put on some breast forms to round things out and I will be damned if it didn't look like I had a woman's body. Then I went into the bathroom to try my hand at makeup.

I didn't have much hope here. I knew something about makeup from taking a theater makeup class once years ago. But I was by no means good at it. But I applied some foundation and I worked from there. I put on some eyeshadow and eye liner and a little blush on my cheeks. It made me look more feminine and feel more feminine. I don't know about passable, but that was not my intent. I followed it all up with a black wig my daughter had for cosplay. With the bangs coming over face, damn, I looked as good as I ever had. Walking around and looking in the mirror, I was extremely turned on. But I still hesitated to touch myself. Why?

I do not consider myself gay. I have never looked at a guy and thought "God I wish I could have that". In fact, I have always been attracted to just women. But when dressing up, the thought of being with a man was intoxicating. Never a particular man, just a man. Some body that I could please.

So here I was dressed on the one day of the year that I could walk out the door and if anybody saw me, I could just say I was going to a party. I thought, it would be great to be out and take a drive. Just to be outside on this warm Halloween night.

This was almost too much for me to take. I had to sit down and calm myself down. But every time, I would start to get myself under control, the thought of going out would return and my breath would leave me. After a while, I decided I couldn't just sit there riding this roller coaster. I got up, grabbed my keys and walked out of the house in a hurry.

The cooler night air settled over me and helped me calm down. It was very exciting, finally out, dressed en femme. I got into my car and started driving. There were still a lot of people and kids walking the neighborhood, yelling and having a great time. Just seeing them relaxed me immensely.

After about a half hour I realized that I was not going to be satisfied just driving around. It was almost ten o'clock and I had no desire to end the night by going home, masturbating frantically then stripping down back into the everyday me. I knew the night life was probably just getting started. I pulled over and thought about what I could do next. I remembered that not too far from my home, there was a bar that I could visit. Close enough to drive to but far enough to not run into anybody I knew.

When I got to the bar, I got a smirk from the doorman. "You look good, Honey." he said, with a funny emphasis on "you". I almost turned around and ran at that point. But I paid the cover with some cash from the purse I "borrowed" from my wife and walked in.

The bar was packed with everything from commandos to sexy nurses and man sized playing cards. There was dance music playing and everyone was having a good time. Or was blitzed out of their minds. Apparently, the party started earlier than I thought. Miraculously, I found a seat at the

bar next to a "cowgirl" (who would get quite chaffed wearing those short shorts on a horse)

I ordered a glass of wine (again trying to be feminine) and I settled back in my seat when it came and sipped my drink. I had no desire to overindulge and try to drive home and I did not want to have to come pick up my car all the way out here in the morning. I started losing myself in people watching when I was startled by a voice near my ear.

"Hi! Do you dress here often?"

I turned to look at the source of this great wit and ended up looking at a pirate. "Hi." I said nervously. I assumed he was quite inebriated and when he realized I was just a guy in drag he would take off. He surprised me. He sat down across from me.

"I'm Dale. And you haven't answered my question."

He had a really cute smirk and a broad chest which was accented by the white tunic he was wearing. He had on a black slash and plastic cutlass and red bandana. I was abashed to realize that I thought he was a really dashing pirate.

"I'm sorry. I don't know what you mean."

Dale laughed, "I'm sorry, I was trying to be cute." I saw how you were dressed, and I wanted to break the ice.

I wasn't sure what to say to him. I just kind of stared for a minute while his exact words swept over me. It occurred to me that he knew exactly what I was, yet here he was speaking to me. Realizing I was being rude I finally replied. " I am SOOO sorry. I really wasn't expecting to speak to anyone tonight. In answer to your question, no, this is my first time here. And if I being honest, it is my first time being "anywhere"."

"Well, that's a shame!" Again, that adorable smirk came out. "You shouldn't have been hiding so long. You have me at a disadvantage now you know."

"How so?"

"You know my name, which I generously offered to you. But you haven't given me any idea who you are."

Honestly, I unsure what was going on. I had to refrain from the impulse to look around the room to see who was watching and laughing. It felt like he was flirting with me. I decided to play along until it got mean. He seemed pretty nice. "I'm Jo..., er I'm Josie. It's nice to make your acquaintance."

"Oh, so formal! Then milady Josie, let me say the pleasure is all mine" He stood up, took my hand, clicked his heels and bowed over my hand.

I couldn't help it, I giggled. And he again gave me that smirk while standing above me. "Well, now that I'm standing up, there is only one thing left to do."

"what's that?" I asked.

"Dance! Come on, let's hit the floor."

My heart starting racing as my flight or...well flight response kicked in. I started shaking my head no and he leaned in close to my ear. "I can tell you aren't pulling my leg and that this is your first time that you are out as yourself 'Josie' and get it you are nervous. But it's Halloween, and nobody cares who you are. And I for one think Josie is one sexy woman, who needs to get up and dance. I won't force you, but trust me, if you don't get up you will go home later and regret at least not dancing."

I turned my head and looked at him, his face not 6 inches from me. I swear I could feel every molecule of air filling my lungs while my heart went pitter pat. I got up and shyly smiled.

"Well lead on then Dale."

It was almost as I had escaped outside myself for a moment. I could see myself being led away to the dance floor where it was thankfully a little dark. I came into my body rapidly as he pulled me in. It wasn't a slow dance song, but the beat worked for dancing close together. Desperately I abandoned my volition as he held me so I wouldn't make us fall while he led.

"You dance really well." Dale whispered loudly in my ear. His lips that close to my neck sent shivers down my spine. I could feel tingles below my butt and in my crotch. Surprisingly, I answered in kind. "Me? I'm just following your lead."

I wish I could say that I stood there and just enjoyed the moment, but I didn't at first. I was too wound up with 'what was going on' and what comes next. Then he pressed closer to me, and I started to get lost in the dance. The masculine smell of his skin. The feel of his rough hands in mine. I realized I didn't want the dance to end but the song did. He started pulling away and I grabbed him and pulled back in. He looked at me with some surprise in his eyes and I said, "sorry" and he replied, "For that perfect moment you should never apologize. Would you like to go sit down and have a drink?"

I thought, oh fuck it. You only live once. And Dale was right, I didn't want to regret the things I didn't do. "I'm guessing you don't live very far away, am I right?"

"His eyebrows shot up, "no, I don't. Just around the corner actually."

"And I'm also guessing that you have something to drink at your place."

Laughing, "yeah, that's a safe bet."

"Well then, why don't we save a little money and go have that drink at your place?"

"Are you sure?" He looked at me with a little concern. I could tell he didn't want to force me into anything I was uncomfortable with. What a gentleman!

"My idea. Yeah, I'm sure." I grabbed my purse and Dale grabbed my hand, guiding me out the door. "I live about two blocks from here," he said, "really just a short walk. But if you have a car and are ok to drive, we can jump in that?"

The cool air felt good against my skin. And the noise abatement from being out of the bar helped me get my head clear. I did not want to get into my car, but I also could picture myself having to do a very awkward "walk of shame". But as nervous as was, I strangely felt more relaxed. Looking at Dale, my I could fell any vestige of reluctance ebb away. I smiled at him, "This is my car here. And I want to reserve it for a fast get-away. I am good to drive. Let's drive to your place." Dale chuckled and opened my door, another first for me. He went around to the other side as I started the car. I turned to look at him as he climbed in the passenger side. "Ok, head down the street to the first intersection and take a left. MY place is about 3/4 a way down the block."

I didn't move for a second. I soaked in the fact that I was sitting next to this very handsome, fit gentleman and it felt like he was going to make all my deepest fantasies come true. I leaned over and kissed him gently on the lips

As I started to pull back, he leaned forward and reengaged, parting his lips and gently flicking my tongue with his.

"I need you to know something," I said as I pulled into the street and started down the road. "I really have never done anything like this before. And I appreciate how nicely you have treated me."

"I believe you," he replied. "And if you don't want to go further, then I understand. I don't want you regretting tonight."

This sent a flutter in my chest, and a stirring in my groin. I never wanted anything so much in my life. "Thanks, but you've been so nice. to me." I think you deserve a reward.

We got to his house, and I pulled into his driveway. We got out quickly and he let me in the front door. He guided me with his hand on the small of my back. The thought went through my head that I wanted his hand lower. "What can I get you?" he asked. "Scotch? Glass of wine?"

"Wine sounds nice, and can I use your bathroom? I'd like to freshen up."

He directed me to his powder room, and I took a long look at myself in the mirror. I didn't know what was going on with me, but I knew I didn't want to stop. I pulled out my lipstick from my bag and re-applied it. Then I took a step back and thought in for a penny...'. I pulled my dress off and looked at the girl in the mirror, dressed in bra, panties and hose with the waist tucked away. My chest ached with lust and longing. I turned around and walked out just like that, leaving the dress behind. I walked back into the living room where Dale was waiting on the couch with my drinks in hand. The look on his face told me I had made the right decision. He was could not stop staring at my body. After a moment, he stood up and walked over to me and handed me my wine. "Oh, my goodness. You are a dream. "He put his hand around my back and pulled me in with one hand and started kissing me. I responded in turn, hungrily offering him my tongue and lips while my back arched into him. My breath catching in my throat as my free hand roamed his muscled chest. I breathed in his masculinity I felt his need rising. Somehow, I open up his shirt and ran my hand down. Down past his abs, under his pants waist and under his underwear. For the first time, my hand touched another man's penis. It was warm and firm in my hand. I could feel it pulsing as I started to slowly jack its length under his clothing. Dale's mouth closed on the pulse in my neck and started to tongue me fervently. "I have never wanted anybody or anything more in my life. I pulled away slightly, downed the wine and put down my glass. Dale just dropped his glass and crushed himself back into my body and lips. My hand pinned between us, gloriously encircled around his member. I squeezed it and was rewarded with a moan in my mouth.

As much as I relished his tongue in my mouth, I could physically feel a desire for more on my tongue I slid down his body to my knees and kissing his dick through his pants, I unbuckled his belt and pulled them off. His beautiful cut, member sprang into my face, and I wasted no time reaching out with my mouth and engulfing his spongy head between my lips. I focused first on just sucking on the head and feeling him pulse in my mouth. After a while I could sense his hips bucking and I started to bob along his shaft. I had never done this, only fantasized. But the fantasy did not match the reality. To be on my knees, in front of a man, pleasing him. My hands grabbing his buttocks and pulling him further into my mouth. The veiny length sliding along my tongue and to my throat. I started to lose control. I wanted more and more. I pushed past my gag reflex and felt him enter my throat. There is no other way to describe the feeling. I felt like a woman. I looked up into Dale's face. His eyes were closed, lost in the moment. I pulled back and started bobbing faster, focusing again on the head. His breath came in sort gasps, and I could feel him tense up. He tried to pull back when he came but I would have none of that. I locked into his spurting cock and swallowed his succulent semen. I wanted his cum down my tongue and down my throat. Some small part of me was wondering what the hell was happening to me. but with his release, I just didn't care. I was lost with cum in my mouth, in my throat and on my face.

I pulled back and wiped my mouth. Dale picked me up and surprised me. He started kissing me. I thought he would be done and would ask me to leave. Instead, he shed the rest of his clothes and led me to his bedroom. He threw me onto the bed and slowly crawled on top of me. My skin was enflamed. Every touch sent shivers into me until he was poised over me and started kissing me again. I know it is a cliche, but I just melted into him and into the moment.

As he lay on top of me on the bed, grinding into my pelvis and my engorged cock, (I can't call it my clit, it's too big) I was amazed to realize that I could feel his member becoming harder. I moaned into his mouth as he was kissing me and ran my nails behind his back. I reached my legs up and encircled his waist and tried to ride him in further into my penis. Pulling back, I smirked, "Somebody is back for more!" He looked me in the eyes, and said, "You are so gorgeous! And I am so hot for you. I just want you to feel like the woman you always desired to be."

I laid there with my hands on his back, my heels on his butt and my breath gone. I was going to need oxygen the way he kept making me swoon. It was one of the most intimate moments of my life and I realized I had to take things further. I had to give this man my everything, I wanted him to own and possess me. I reached down and I scooted out of my panties and kicked them off the bed. I pulled my legs up to expose my glorious, aching hole and I told Dale, "Take me. Fill me with you cock and pour yourself into me. I want you in me and need you to erase for a time anything else I have ever been."

He didn't insult me with a 'you're sure'. The look in his eye told me he couldn't have refused me if the house was on fire. He kissed down my body and started tonguing my ass. Leaving great trails of saliva on my thighs and running between my cheeks. He came back up quickly and used some more spit to lube up his dick. I looked down as he did it. His hand running up and down his length. His circumcised head glistening. I put some saliva on my hand and replaced his. Feeling the hard sponginess. Marveling at his warmth. My mouth started watering but I let it go and he pulled my legs up to better expose my hole. I felt his penis gently come to rest against my sphincter. I bucked my hips to increase the pressure. I wanted it now. I needed to cross that threshold. He pushed his hips forward and slowly entered me. I won't lie, I have played with objects down there before, but this still hurt. But my need overrode my pain and before I knew it, his entire shaft was up my ass. I relaxed and I could feel the pain ebb. I kissed him again and whispered, "Fuck me." He quickly obliged and pleasure started to emanate from my very center. I don't know how long it lasted. I remember the drive of his rod into me, over and over. The feel of his muscles in his arms as he held himself over me. My moans mixing with his pants of exertion. He became covered in sweat, and I did too. I could feel my climax building with every thrust. My rigid penis rubbing between our two bodies. I screamed out his name as I came in buckets between us, whimpering and shaking through one convulsion after another. I peaked again a minute later feeling him tense up and feeling his semen spurt into me. Filling me up like the good little slut I wanted to be.