CD03 - James
Code: MM

James was different than the other guys I had met online.  He wasn't into getting all dressed up in women's clothes.  He was just a straight laced guy that was looking for some fun with another guy.  He was however, extremely intrigued by the idea that I would dress up and play with him.

Our email conversations were, of course, different from the ones I had with other guys.  We didn't talk about the clothes, or the feel of the material, or where we got them.  Rather, with James, we talked more about me wearing them and giving him a fashion show.  They tended toward thoughts of me acting the role of the woman.  He wanted to "date" me like he would any other woman.  He wanted to bring me to his room, and watch me as I knelt before him and took him in my mouth; he wanted to be surprised when he lifted my skirt and found not a pussy but a hard cock.

I indulged his fantasy whole heartedly; it was one of my own too!  

We talked for weeks online, passing emails back and forth daily.  After many unsuccessful attempts in making plans to meet, the day finally arrived.

Striving for anonymity and discretion, I did not arrive dressed as a woman, but rather in my standard attire - Dockers, shirt, panties and pantyhose! Outside, every bit the man, inside every bit the woman trying to get out!

I drove into the parking lot of the hotel where we had decided to meet. Up until then, my nerves were pretty calm - "just another day" I kept telling myself.  Except that on this day, I would be playing the part of a woman, and who knows what I will be doing in about 15 minutes from now!!!

I had James' cell number, we had exchanged them during our last emails while planning this event.  I dialled the number.  I knew James was older than me, by six years; but that didn't bother me at all.  

The phone rang twice.  I started to think the number was wrong, or that he had changed his mind.  After the third ring, I was ready o hang up, when I heard a deep voice say: "Hello"

"James", I asked politely

"Yes", his answer brief and to the point.

"It's me Jerry", I offered

"Oh, Jerry, sorry I wasn't sure and didn't want to say anything until I knew it was you!" he said excitedly, "I'm checked into room 406" he continued.

"No problem, I'll be right there" I said, and hung up the phone.

After I hung up I realized that I didn't know if he was waiting for me in the room or in the lobby, we really hadn't discussed it much before.  I guess if I ever do this again, I really will need to pay more attention to the details.  I seemed to have allowed my cock to make all these arrangements, and apparently cocks don't do well with details!

I grabbed my bag, slung it over my shoulder, and headed for the door.  An air of determination about me, and a bead of sweat forming on my forehead.  

As I got to the door, I noticed the lobby was full of people.  "Well Duh" I thought "It is 9:30 in the morning!"

The realization that someone I know might be beyond the door, stopped me dead in my tracks.  The half hour drive over, the phone call, the confident march to the door was all over now.  The reality of what I was about to do had finally hit me.  I took a deep breath, and briefly flirted with the idea of turning around and going home. Again, my cock made the decision for me! With somewhat renewed confidence, and a forehead dripping sweat, I entered the building.

The lobby was full of people.  Many were at the front desk obviously checking out; a number of people were moving around the breakfast buffet in the corner; and a small group of six or seven were seated in the lounge area by the front windows.  I ignored the people at the desk, and those in the buffet.  If James was waiting for me in the lobby, he would be in the lounge area or waiting by the elevators.

I gave a quick glance around looking for the elevators; and I quickly realized I needed to pass by the lounge to get to them.  Again with renewed "cocky" confidence, I moved toward the elevators.  As I passed the lounge, I noticed one man was sitting alone close to the path I needed to follow.  His eyes met mine.  I remember thinking that he wasn't very good looking.  

In all the time that I had thought about this meeting, I had never seen James' face, and had always pictured someone tall and handsome.  In hindsight I guess we all do that when we go out on a blind date.  This was no different.  I kept looking at the man in the chair as I passed.  I thought about stopping and asking him if he was James, but I quickly thought differently.  If this was James, then he would probably realize it was me, and get up and follow me to the elevator.

As I came closer to him, I smiled.  If it was him, then great, if not then I was at least being polite.  Besides, he was staring at me too.

He gave a brief smile and a nod; but he made no move to get out of the chair.  On reaching the elevator, I pushed the button, and took a quick glance back. The man had returned to reading his paper.  I felt a bit of relief thinking that this not-so-handsome man was not my target for the day, "phew".

I entered the elevator after a woman who was also waiting.  I asked her floor, and pushed the buttons.

She kept looking over at me, but I tried not to catch her eye.  My nerves had started a full blown sweat on my forehead.  The last thing I needed right now was to talk to someone in what I'm sure would have been a very broken and parched voice.

She exited on the third floor, and the doors closed again.  I started some deep breathing and wiped my forehead with a small towel I pulled from my gym bag.  The doors opened on four, and I stuffed the towel back in the side pocket.  A bit more breathing and I was ready to move.

It wasn't a very long walk to 406, but it certainly felt like hours.

Reaching the room, I took another breath and fought another urge to turn around.

"This is it" I thought, "I am about to engage in something that I have only every dreamed about." I knocked on the door.

Within a couple seconds, I heard the click of the lock, and the door started to move inwards slightly.  I caught a glimpse of his face when I heard "Jerry?"

"Yes, it's me" I answered

He opened the door fully, and invited me inside.  

My lead feet finally moved and brought me inside.  Looking around, I saw a standard room with a bed and desk.  The curtains were open, and the light of the morning sun was blazing through.

I turned around dropping my bag on the suit case stand as he locked the door and se the latch.  I assumed he had put out the "Do Not Disturb" sign too.  

Turning in, he faced me.  He was giving me the once over, two and three times.  Each time his smile grew a bit more.  He liked what he saw.  For me, I still didn't see the handsome man I had imagined, but it was certainly better that what I found in the lobby.  I certainly could not complain.  

Approaching me, he said "I thought of waiting until you had a chance to get dressed up, but I can't help myself.  Do you mind if I kiss you?"  He asked.  Impressed by his politeness, I could only respond "I wish you would!"

He gently took me in his muscular arms, and held me tight.  He placed a gentle, tentative kiss on my lips and pulled back a bit.  He was watching for my reaction.  I'm certain a million questions were running through his mind.  I'm sure he wondered if I liked the kiss, if I wanted more, if I was even going to continue with our "date".  I gave him the answer to every question he had by slightly tilting my head to one side. Turning his head the other way ever so slightly, he pulled me close again taking my mouth full on his.

We kissed and kissed and kissed for what seemed like days! Switching the tilt of our heads, and holding each other in a giant hug, we continued our kiss.

My arms were tight around his neck, holding my lips to his.  I started to feel his hands moving over me; down my back, then around to my crotch.  He was rubbing his hand over my hard cock.  I think I heard him moan.

Slowly we pulled our lips apart, and he pulled my head into his shoulder and caressed my back and neck with his strong hands. "Shall we get undressed now?" he asked, again being ever so polite. 

"OK", I responded, and then added "What would you like me to wear?" 

He didn't respond right away, but I could tell he was looking at my bag.  I pulled away a bit, and almost as an after thought, I stretched my face back to his and gave him a peck on the lips.

We pulled apart, and I asked if he would close the drapes.  He complied. Then we started to undress ourselves.  This is not really the way I had imagined it, but never having done anything like this before, I really wasn't sure about the protocol.

I watched him for a bit. When he was standing there in his underwear I started to undress; first removing my shirt, then my pants.  I stood there wearing blank panties and red tights. 

"Very nice" he commented.

I fished through my bag searching for something.  I realized that I had not planned this too well either.  After struggling a bit with "what should I wear", I decided and pulled out my red dress,
 
"A girl needs a private place to dress" I said and went into the bath room.  I put the dress on and checked myself in the mirror.  "What the fuck was I doing" crossed my mind, but my cock quickly pushed the thought aside, and I smiled at myself and went back into the room.



From the instant he saw me; his eyes ran me up and down again. Like before, his smile widened with every pass.  This time, I could feel his lust pouring over me.  He had removed his shorts while I was away.  His cock wasn't very big, but I wanted it anyway!  I couldn't tell if he was fully erect or not.  "If that's as big as it gets", I thought, "he might want to try a Viagra!"  I giggled to myself, all the time smiling at him and darting my eyes down to his cock every so often.

"I love your dress" He said softly as he came over to me.

We embraced in another kiss, this time his hand went straight to my crotch, rubbing me through the dress.  I too got in on the action, and wrapped my hand around his member.  It got a bit harder in my hand, but was certainly still softer than mine.

He noticed this too; and breaking our kiss briefly he said "You are so hard! I want to touch it"

I just brought him back into the kiss.  I started to feel his tongue probing at my lips, and I gently parted them to let him in.  We played with each other's tongues. I was enjoying the new feelings I was experiencing, a man's tongue in my mouth; and his cock in my hand. 

I was stroking him when he said: "You have to stop or I'll cum right now."

I didn't want to stop rubbing his cock, but I did.  I knew deep down that I wanted to suck this man's cock and have him cum in my mouth.  I let his cock go, and put my arms around his neck; kissing him once again.  His hands were busy trying to lift my dress to get at my cock.  Of course, he was doing this while trying not to break the erotic kiss we were sharing.  My dress was rather form-fitting so it took him a bit of trying, but he soon got his hand under my dress and onto my tights covered cock.  He didn't seem to try to get in my tights or panties; I guess the feeling of the material and my hard cock was what he was looking for.

I started to feel some stirrings in my balls, and thought I best move on with this or I too may cum early.  I broke away from his lips and started to kiss my way down his chest. Soon I was on my knees and face to face with his cock.  Grabbing the member at the base, I directed it toward my lips and gave it a small kiss. I could tell he was enjoying this by his moans.  I began to lick his entire cock and soon I started to cover it with my mouth.  The feeling of his cock in my mouth was unreal; I could not believe it was me doing this.  It was almost as if I was disconnected from my body watching this.  Snapping back, I realized that it was infact my mouth that was rubbing its way up and down this cock.

I was getting into the groove, and working my tongue on the sensitive part right on the bottom side of the head; when I heard him moan loader and say "Do you want me to cum in your mouth?"  I knew the answer to that question without even thinking; and let him know by moving my mouth lower on his cock and tickling it more vigorously with my tongue.  He didn't say anything more, but rather placed his hands gently on my head.  Within a couple seconds I felt his cock become stiff than ever that day, and soon his warm cum started to pour into my mouth.  I really didn't know what to expect, I had heard that it could come out so fast that it would shoot down my throat, but this was just a gentle filling of my mouth.  I took his entire load without any difficulty at all.  I guess it was his age, but I certainly wasn't complaining.  When his spasms had stopped, I rubbed it from the base up, gently sucking to get every drop.

His cock became limp very quickly, and I allowed it to fall from my mouth, being very careful not to lose any of the cum.

James helped me stand up.  I held my mouth open for him to see the beautiful cum he gave me.  His smile grew.  I wasn't sure what he would do, but I was wishing for him to kiss me so we could share this wonderful feeling.  He only gave me a peck, lightly touching my lips with his tongue. I didn't mind, more for me. 

"I won't mind if you want to spit it out" he said in a caring voice.

I think I surprised him; I think I surprised myself too, by swallowing the entire load without any thought or ceremony.  

"No thanks" I said, in answer to his question.

He laughed and said "No one has ever swallowed my cum before, my wife always spits it out.  That is when she let's me cum in her mouth!"

I joined his laughter.  When he said "I want to suck you now!"

He pushed me back gently to the bed.  I laid back, and he lifted my dress past my waist.  Taking the hem of my tights and panties, he pulled them both down to my knees.  Within seconds he was ravaging my cock like a dog on a bone.  He was fierce in his approach, but very gentle in his actions.  

I was starting to enjoy his attention; when suddenly I started to realize what I had done, and what I was doing.  "O my god, I just sucked a cock!" I thought "what does this mean, what now?"  My thoughts started going wild streaming pictures of my life and family through my head.  My breathing started to increase, my heart started to race. I was in full blown panic.

I managed to get my head straight, but I knew that I had to get out of there.  I didn't realize it, but this whole time my cock was going limp, despite the fact that it was being sucked by this man's mouth.  He noticed this immediately and said "Jerry, are you OK?"

"No" I responded

"Do you want me to stop?" he asked

"No, but I think you should" I answered sadly

He let me go, and moved up beside me on the bed. He ran his hand gently over my dress covered chest, saying: "Sometimes it's so intense that when you come down you start to panic."  I looked at him, he was right, but I couldn't tell how he knew.  He continued talking "I've been there.  It was the first time I sucked a cock.  I understand"

I could not believe this.  Here I was dressed as a woman; I just enjoyed sucking James' cock and the awesome feeling of his cum filling my mouth; and then swallowing all of it.  I could not believe that now, while this man was sucking my cock, I panicked.

I wanted to leave, but I didn't want to just run away. I really didn't know what I wanted, but I knew that I did not want to make this man feel any worse than he probably does now.

I guess he saw the confusion on my face, because he just said "It's OK".  I looked at him, and saw the concern in his eyes.  He was not mad at all. In fact he appeared to be very concerned for me.  He continued, "If you want, we can stop for today, and maybe pick this up again another time."

I was shocked and relieved at the same time.  All I could muster was "I'm sorry"

"Don't worry about it, we can get together anytime when you are ready.  This is heavy stuff" He said.

I guess my nerves finally got the best of me.  I grabbed my stuff and got changed back into my regular clothes.  After another quick kiss goodbye, I left.  It was not until I was halfway home on the highway that I looked at the clock.  I couldn't believe it, but I could not have been in the room much longer than twenty minutes.  

That evening, I was home safe and sound, watching TV and thought I may never see this man again.  If it was me, I probably would never call again.  I felt a bit sad and a bit relieved; but also very happy that I had finally known the feeling of having a cock in my mouth and the taste of another man's cum.  I hoped that I could do it again soon.

