My Qualifications to Write About Crossdressing
- 2 years ago
- 36
- 0
I Was His Bitch (first Time Crossdressing) free porn video
My growing curiosity was really starting to take control. I've spent so many years married, hiding my true thoughts and fantasies about sex.
My wife and k**s were going out of town a couple of weeks ago and I was going to explore more of what I wanted. As the day they were going to leave got closer, my pulse would race and my palms would sweat.
I just hoped I wouldn't chicken out.
Finally, I dropped them off at the airport and as soon as I did, I was freaking out. Just thinking about visiting my first gay bar made me have an erection so hard, I unzipped and released the pressure in the car on the way home.
As soon as I got to the house, I ran inside and started getting ready.
I shaved, had my shirt and pants picked out and with a splash of cologne, I waited for the bar to open.
I knew it opened at 7pm, so I waited until 8 to finally get in the car. I was so nervous driving there!!
As I pulled up, I noticed a couple of pretty young guys walk in.
I started to doubt whether I should go in. Should I just leave this as a fantasy? I'm a middle aged guy with a slight ponch and thinning hair. What if no one was even interested in me. That would be devastating.
But I gathered up my thoughts and figured, "If nothing happened, at least I would know."
As I walked in, I showed the doorman my ID and noticed my hand was shaking.
I went straight to the bar and ordered a beer to calm my nerves.
About a half hour went by as I sat watching people dance, talk, laugh and have fun. I stared at my drink occasionally and tried to figure out whether I should go.
Suddenly a guy about my age walked over to me and introduced himself. He said his name was Fred and he noticed me when I walked in.
He wasn't bad looking. A little chubby with a goatee.
We talked a while about jobs, etc. and then suddenly he put his hand on my knee, looked me in the eye and said, "How about we get out of here?"
I bolt of lightening ran through my body as I shakily said , "OK."
He said he didn't live to far from there and would I like to follow him home? I agreed and we both went to our cars.
I followed his car to an apartment complex about a mile away.
As I got to the door, he put his key in and as he opening the door, he looked over and said, "I'm glad you came. I was worried you would say no to me."
I walked in and noticed how nice the place was. Very neat and tidy.
I turned to see him shut the door when he walked right up to me quickly, placed his hand on the back of my neck and pulled me in for a kiss.
It was long and deep. The deepest kiss I'd ever been given. Our tongues wiggled in each others mouths for what seemed like an eternity. He grabbed my butt and pulled it in close. I could feel his throbbing cock through his pants as it touched my stomach.
He slowly pushed me against the wall and kissed me more, pushing his body more against me.
He finally stopped and said, "Sorry. I just....I just couldn't help myself."
I licked my lips and told him it was fine. I liked it.
"Are you ok if I sort of take over?"
I told him I was very new to this and yes, I wanted to learn whatever he needed to make him happy.
He looked at me and said, "Anything?"
I started to get a little worried and whispered, "Well...no Anything."
He smirked and said, "No, nothing bad, just...would you mind if I gave you something to wear?"
"No, not at all. ", I said.
He disappeared for a about 3 or 4 minutes and then came out with something blue and silky. "What size shoe do you wear?"
"Um....11."
"ok,", he said. "I think these will fit."
He then gave me what appeared to be a dress and shoes.
"I used to play dress up and well, It'd be great if you would wear these."
I'd only dressed as a woman once before and that was just trying on a girls bathing suit during a sleepover. This was way, above and beyond, but as I saw the huge bulge in his pants, I really wanted my lips around his cock, and now, I was willing to do anything.
"OK", I said. I'll be right back.
I walked into his bathroom as he told me where the bedroom was and that he'd be waiting.
I walked in, shut the door and looked at the dress. It was pretty. Low cut and silky smooth.
I slipped off my clothes and put it on. I then put the shoes on and yes, they did fit. They were high and I'd never walked in high heels before, but got the hang of it pretty quick.
I walked out and shut the light off. I noticed a dim light coming from where he said the bedroom was and started towards it.
There he was, laying under the covers, a tent from the bedsheet where his penis was.
I walked to the end of the bed, put my hands on the sheet and slowly crawled towards him.
I ran my hands over the sheet to his manhood and slowly played with it, letting the sheet smoothly rub on it.
He threw his head back and moaned a little, "yes".
I crawled up further until my ass was over his bulge. I moved the dress to flow around me and laid my cheeks over his cock, letting it slip between them.
I rocked slowly back and forth as a pinned his arms down.
I could feel him pushing up against me with his hips.
After a while, I let his hands go and pulled the sheet down over his cock.
There it was, throbbing and ready.
I slid my lips over the sides of it for a couple of minutes and then finally, quickly put the whole thing in my mouth.
"GOD, YES!" he said.
I cupped his balls and moved up and down with my mouth. He grabbed my hair with both hands and started fucking my face. Harder and harder, moaning louder and louder.
"Wait, wait, wait!", he said. "I'm gonna cum too fast."
He then grabbed my leg and pulled me over his face, putting my cock into his mouth.
I was sixty nine-ing!
It felt so good to finally let go. To be myself. To have this man sucking my cock as I sucked his. Not a care in the world.
"Cum in my mouth!", I said as I grabbed the bottom of his shaft, putting his head in my mouth.
"Oh, thank you!", he screamed.
It only took a couple of jerks for him to explode his warm cum in my mouth. I didn't think twice. I just quickly swallowed what I could and let the rest run down my face.
The thought of him cumming made me cum and he had me shoot it on the pillow.
We laid there for a while, tired and sweaty.
As I got up, he also got up, came around to my backside and wrapped his arms around my belly.
He kissed my neck and whispered "thank you" in my ear.
I reached back and held his member, which was already hard again.
I slowly rubbed it as he held me.
It felt so strange wearing a dress and heels as a man held me close, but it also felt so good. In that moment, I was his. I was his love doll and I told him if there was anything else he wanted, I'd do it.
He told me to bend over the bed and I did.
I knew what he wanted and I wanted it bad.
He went to retrieve something from the desk by the bed and then came back.
I felt the dress lift up over my ass. A slow, slightly cold liquid ran down my ass crack as he messaged it in.
Then I felt it.
The tip of his cock was in my hole. Not a lot, but enough to feel it.
He slowly started pushing it in and I twisted and turned to make it happen.
He was finally in about halfway.
It hurt, but it felt so good.
I looked down and saw my feet in those high heels and was more turned on than ever.
I was his woman and he was fucking me.
"Grab my ass", I told him.
He grabbed both sides and began pumping harder and harder.
"I'm gonna come again.", he said.
"Good. Make me yours!" I yelled. I didn't care if anyone heard me. I wanted his cum inside me.
Then I felt it. It's warm ooze filling in my hole. He grunted and groaned behind me until it was finished.
My legs were jelly and I had to lay down on the bed, but it was the best I'd felt after sex in a long, long time.
I filled with his cum, laying on his bed in a dress and heels.
I laughed a little, wondering what my wife was doing right now and if she had a dress like this.
My wife and k**s were going out of town a couple of weeks ago and I was going to explore more of what I wanted. As the day they were going to leave got closer, my pulse would race and my palms would sweat.
I just hoped I wouldn't chicken out.
Finally, I dropped them off at the airport and as soon as I did, I was freaking out. Just thinking about visiting my first gay bar made me have an erection so hard, I unzipped and released the pressure in the car on the way home.
As soon as I got to the house, I ran inside and started getting ready.
I shaved, had my shirt and pants picked out and with a splash of cologne, I waited for the bar to open.
I knew it opened at 7pm, so I waited until 8 to finally get in the car. I was so nervous driving there!!
As I pulled up, I noticed a couple of pretty young guys walk in.
I started to doubt whether I should go in. Should I just leave this as a fantasy? I'm a middle aged guy with a slight ponch and thinning hair. What if no one was even interested in me. That would be devastating.
But I gathered up my thoughts and figured, "If nothing happened, at least I would know."
As I walked in, I showed the doorman my ID and noticed my hand was shaking.
I went straight to the bar and ordered a beer to calm my nerves.
About a half hour went by as I sat watching people dance, talk, laugh and have fun. I stared at my drink occasionally and tried to figure out whether I should go.
Suddenly a guy about my age walked over to me and introduced himself. He said his name was Fred and he noticed me when I walked in.
He wasn't bad looking. A little chubby with a goatee.
We talked a while about jobs, etc. and then suddenly he put his hand on my knee, looked me in the eye and said, "How about we get out of here?"
I bolt of lightening ran through my body as I shakily said , "OK."
He said he didn't live to far from there and would I like to follow him home? I agreed and we both went to our cars.
I followed his car to an apartment complex about a mile away.
As I got to the door, he put his key in and as he opening the door, he looked over and said, "I'm glad you came. I was worried you would say no to me."
I walked in and noticed how nice the place was. Very neat and tidy.
I turned to see him shut the door when he walked right up to me quickly, placed his hand on the back of my neck and pulled me in for a kiss.
It was long and deep. The deepest kiss I'd ever been given. Our tongues wiggled in each others mouths for what seemed like an eternity. He grabbed my butt and pulled it in close. I could feel his throbbing cock through his pants as it touched my stomach.
He slowly pushed me against the wall and kissed me more, pushing his body more against me.
He finally stopped and said, "Sorry. I just....I just couldn't help myself."
I licked my lips and told him it was fine. I liked it.
"Are you ok if I sort of take over?"
I told him I was very new to this and yes, I wanted to learn whatever he needed to make him happy.
He looked at me and said, "Anything?"
I started to get a little worried and whispered, "Well...no Anything."
He smirked and said, "No, nothing bad, just...would you mind if I gave you something to wear?"
"No, not at all. ", I said.
He disappeared for a about 3 or 4 minutes and then came out with something blue and silky. "What size shoe do you wear?"
"Um....11."
"ok,", he said. "I think these will fit."
He then gave me what appeared to be a dress and shoes.
"I used to play dress up and well, It'd be great if you would wear these."
I'd only dressed as a woman once before and that was just trying on a girls bathing suit during a sleepover. This was way, above and beyond, but as I saw the huge bulge in his pants, I really wanted my lips around his cock, and now, I was willing to do anything.
"OK", I said. I'll be right back.
I walked into his bathroom as he told me where the bedroom was and that he'd be waiting.
I walked in, shut the door and looked at the dress. It was pretty. Low cut and silky smooth.
I slipped off my clothes and put it on. I then put the shoes on and yes, they did fit. They were high and I'd never walked in high heels before, but got the hang of it pretty quick.
I walked out and shut the light off. I noticed a dim light coming from where he said the bedroom was and started towards it.
There he was, laying under the covers, a tent from the bedsheet where his penis was.
I walked to the end of the bed, put my hands on the sheet and slowly crawled towards him.
I ran my hands over the sheet to his manhood and slowly played with it, letting the sheet smoothly rub on it.
He threw his head back and moaned a little, "yes".
I crawled up further until my ass was over his bulge. I moved the dress to flow around me and laid my cheeks over his cock, letting it slip between them.
I rocked slowly back and forth as a pinned his arms down.
I could feel him pushing up against me with his hips.
After a while, I let his hands go and pulled the sheet down over his cock.
There it was, throbbing and ready.
I slid my lips over the sides of it for a couple of minutes and then finally, quickly put the whole thing in my mouth.
"GOD, YES!" he said.
I cupped his balls and moved up and down with my mouth. He grabbed my hair with both hands and started fucking my face. Harder and harder, moaning louder and louder.
"Wait, wait, wait!", he said. "I'm gonna cum too fast."
He then grabbed my leg and pulled me over his face, putting my cock into his mouth.
I was sixty nine-ing!
It felt so good to finally let go. To be myself. To have this man sucking my cock as I sucked his. Not a care in the world.
"Cum in my mouth!", I said as I grabbed the bottom of his shaft, putting his head in my mouth.
"Oh, thank you!", he screamed.
It only took a couple of jerks for him to explode his warm cum in my mouth. I didn't think twice. I just quickly swallowed what I could and let the rest run down my face.
The thought of him cumming made me cum and he had me shoot it on the pillow.
We laid there for a while, tired and sweaty.
As I got up, he also got up, came around to my backside and wrapped his arms around my belly.
He kissed my neck and whispered "thank you" in my ear.
I reached back and held his member, which was already hard again.
I slowly rubbed it as he held me.
It felt so strange wearing a dress and heels as a man held me close, but it also felt so good. In that moment, I was his. I was his love doll and I told him if there was anything else he wanted, I'd do it.
He told me to bend over the bed and I did.
I knew what he wanted and I wanted it bad.
He went to retrieve something from the desk by the bed and then came back.
I felt the dress lift up over my ass. A slow, slightly cold liquid ran down my ass crack as he messaged it in.
Then I felt it.
The tip of his cock was in my hole. Not a lot, but enough to feel it.
He slowly started pushing it in and I twisted and turned to make it happen.
He was finally in about halfway.
It hurt, but it felt so good.
I looked down and saw my feet in those high heels and was more turned on than ever.
I was his woman and he was fucking me.
"Grab my ass", I told him.
He grabbed both sides and began pumping harder and harder.
"I'm gonna come again.", he said.
"Good. Make me yours!" I yelled. I didn't care if anyone heard me. I wanted his cum inside me.
Then I felt it. It's warm ooze filling in my hole. He grunted and groaned behind me until it was finished.
My legs were jelly and I had to lay down on the bed, but it was the best I'd felt after sex in a long, long time.
I filled with his cum, laying on his bed in a dress and heels.
I laughed a little, wondering what my wife was doing right now and if she had a dress like this.
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