First time in full on cross dressing

From my last story, Fred, the man I met at the gay bar, contacted me again a while ago. He said he couldn’t stop thinking about me. He told me had had other one night stands, but felt very comfortable with me. I was pretty flattered to say the least. Compliments are few and far between when you get to be my age.
He told me he’d like to see me again. My heart started to race a little. I mean, this is still all new to me and suddenly I have a regular thing?
He said he had some down time during the weekend and wanted me to come see him.
I admit, I thought about it for a while. I mean, I’m married. I can’t have something going on on a regular basis, but the thought of his cock got me getting hard again and I couldn’t help it. The tabboo of it all had me almost cumming in my pants. I agreed to see him and we found a hotel midway between us.
As I was driving, he texted me that he had already gotten a room and to meet him there. I pressed the gas pedel a little harder.
When I got there, I took a deep breath and thought again, “Is this what I wanted?”
Again, the thought of his dick sliding in and out of my ass got me horny again. There’s a pleasure a man can give that a woman just can’t, so I knocked.
He opened the door and welcomed me in. As I walked past him, he put his arm around my waist and said, “I have something special for you to wear in the bathroom. I hope it fits and I hope it ok.”
I turned to face him and he was smiling so big, his raging huge boner was practically coming out of his jeans.
I went into the bathroom and found a small paper bag on the counter next to a pair of opened toe high heels.
I looked in the bag and saw it was a dress, complete with nylons.
He wanted me to put this on?
I felt the dress. It was so smooth. Like silk. It felt really good rubbing around my hand, it HAD to feel good rubbing on my ass, right?
I stood there for a while and finally thought, “SCREW IT! YOU ONLY LIVE ONCE !” and began to put out on.
I slipped the dress over my head instead of unzipping it. It felt so smooth and cool against my skin. I then sat down and put the knee high pantyhose on. Luckily the shoes fit. I felt he had maybe done this before.
I looked in the mirror and I’ll admit, I felt a little ridiculous. Was this what he wanted?
I walked out and saw him laying on the bed. He had a wig laying next to him. “Is this too weird?”, he asked.
I told him, if this was what he wanted, I would be more than happy to help. I put the wig on, which was a bushy blonde type color.
“My, God.”, he whispered. He then walked around me, looking me up and down. Then I felt him come up behind me, wrapping his arms around me and pushing his cock into the crease of my ass.
I’ll admit, I felt….. Beautiful.
He spun me around and kissed me, forcing his tongue deep into my mouth, his hands caressing my silky ass.
He kept pushing his cock into me. I took hold of it and started stroking it as we kissed. He finally stopped, put his head on my shoulder and moaned.
My turn.
I slowly kissed my way down.
Finally, I got on my knees and started slowly stroking his cock with my fingers. I licked the edge of it, up and down. He put his hands on my head and tried to push me on his dick, but I wasn’t ready. I wasnt through teasing.
After about 3 minutes of cock teasing, I licked the head a couple of times, then went in deep, putting his full, hard cock in my mouth.
I remembered the first time we were together. It was a wonderful feeling. We fully trusted each other to pleasure ourselves. His familiar cock sliding in and out of my mouth.
He pulled out, took my hand and led me to the bed. He laid down and pushed my head to his cock again.
I went faster and harder this time, wanting him to cum.
He was about ready to when he stopped me.
He then pulled my head up, took his arms and put me into a doggie style position. I felt him slide the dress up over my ass, then some cool liquid pouring over my ass. He was lubing me up good.
He placed his hands on the small of my back and started to enter.
It hurt at first, but it was a strange hurt. I loved it. The thought of him all the in had me so excited.
After a few more tries, HE WAS IN!
I was being fucked like a woman. In full women’s clothing, complete with heels. This is how a woman felt.
He grabbed me harder, thrusting in and out. I could feel his balls hitting my ass. I reached back and grabbed his hips, holding him in. Sweat dripped as he kept thrusting in and out. I held myself up, feeling my own hard cock sliding around the dress. Steady and smooth, we fucked as one. Both of us swaying at the same time.
That was enough for him as he finally came. I felt the hot liquid squirt inside me and drip out.
He collapsed behind me, saying that was the best sex he could remember.
Again, TOTALLY flattered.
He remarked how I hadn’t cum yet, so he rolled over and sucked me off. It felt good, but not as good as giving him the pleasure of being his bitch.
I stood up and started to walk to the bathroom to clean off, when I noticed the city lights cracking through the curtain. It was dark now, so I opened them to look. We were on the 9th floor and the view was fabulous.
Suddenly I felt familiar hands wrap around me and caress my cock. He rubbed it until it was hard, then slowly started lifting my dress again.
I felt his hot, throbbing cock once more start to force its way into my ass again.
I leaned forward and put my hands on the window sill. He slipped in easier this time and again, started fucking me harder with his cock, his hands steady on my hips.
I looked out at the city, feeling the head of his member sliding in and out, over and over.
What a beautiful site and what a great feeling.
We were both harboring a secret affair, but having sex right in plain view of the window.
“Do it!”, I said. “Cum in me again, right in front of everyone.”
He trusted harder and harder. I groaned and groaned.
Groaning in extasy.
Finally he came, oozing out my ass, pushing me against the glass.
As we rested for a moment, I finally stood up, knees weak.
He held me up, wrapped his arms around me and kissed my neck.
“Thank you.”, he said.
I turned and kissed him hard on the lips, feeling the dress press against me again.
I then went into the bathroom and showered, washing all the cum off me.
As I came out, he was dressed also. We kissed before opening the door, then went our separate ways.
I will admit, it was a 30 minute drive back to my house and wacked off while driving to ease her another erection.

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