This is a print version of story My first meeting with Henry - Story 2 by hotcdsub from

My first meeting with Henry - Story 2

Background: Me - Closet bi-crossdresser (Katie) - 48 yo 5'11" 185 fit; smooth all over; office manager. Quite passable except voice, sexy, attractive, submissive and horny. Only wear dresses, no jeans or skirts. Try to be a girly girl. Black lace thigh highs, red and black lace teddy, black lace panties, long auburn wig, black open toe heels, bright pink nails. Him (Henry) - 43yo construction worker 6'1" 195 toned 8 1/2" uncut muscular fat veiny cock groomed naked.

As Henry opened the door to his house, we said hi and I proceeded to walk away across the room, my short black dress, black stockings and lace panties barely hiding my goodies. My long auburn wig flowing, my ass cheeks moving gently as I walked in my open toed 4" heels. "Wow", he said as he eyed me up. A total transformation from last evening at the bar and last week when I first pleasured him.

I turned and asked if he wanted some of this subservient slut ass! I put my hand on one ass cheek and bent over a little, lifting part of my dress to reveal my vibrating butt plug. Henry snapped, "get back over here slut.” He told me last night that he had some fun ideas for today.

I lowered my eyes and walked back to him since he is the boss and man in this sexual relationship.

Then he took my hand and led me to the couch. The same couch where last week I sucked his cock and swallowed his cum. I wrapped my arms around him and gave him a long passionate kiss, my red lipstick transferred to his lips, our tongues intertwined. I unzipped his fly and reached in to feel his stiffening fat cock.

I gently stroked and squeezed his penis as it began to get harder. My heart was beating fast since I was so excited to be dressed for him and felt so sexy and submissive.

He broke the kiss and whispered in my ear, "Now bitch, walk over to the door, get down on your knees and crawl back to me. When you get here, I want you to suck my cock.”

I was excited and did as he commanded, I pulled down his pants and his large mushroom headed hard cock sprang out. His foreskin pulled back. I looked up at him and said that I loved his hard cock! I rubbed his penis all over my face. He was d***k last week and shot in about 5 minutes. Hopefully today he would last longer.

His precum was glistening and I was panting. I grabbed his asscheeks and slowly begin licking his balls, then moved to the underside of his shaft and licked all the way up to the precum. I stuck my tongue in and licked it up.

I opened my mouth and took his head in, then his whole cock slid down my throat. Last week, I could get all but the last inch in. Now it all went down my throat! I had been practicing deepthroat techniques during the week with dildos and it paid off here.

He let out a moan of pleasure and I think I smiled with his cock buried past my tonsils. He put his hand on my throat and felt his penis sliding in and out. He then began face fucking me.

I continued sucking him when he picked up a flexible leather paddle. (His former girlfriend was into bondage so he had some items left from that relationship.) He proceeded to pick up my dress and began paddling my cheeks. His cock was still buried in my throat and with each smack the sucking got stronger. He was ready to cum, but said, "Stop sucking my cock slut.”

He removed my dress to reveal a sexy red and black teddy. He pulled down the cup from each tit and placed clover clamps on my fat nipples. He then grabbed the chain of my nipple clamps and made me stand up and we kissed some more. His hands began caressing and squeezing my asscheeks and I felt his wet, engorged cock against my stomach.

This was heaven I thought. A man with a big cock taking control of my body. Who would have have thought this could happen having only known him for a week, yet I was living it and loving it!

He put me over his knee and began paddling my smooth asscheeks, then he rubbed my reddened cheeks. He told me not to touch his cock until told to do so. I tested him and he spread my legs f***efully and laid out a hard smack on my right ass cheek. His cock was twitching and I felt its heat on my hip.

Then he pulled down my lace girly panties and smacked my balls. He grabbed them, squeezing the sack and gave them the full attention of the leather paddle. I was in painful pleasure and loved it.

My balls were aching from the abuse they had taken and then Henry pulled out some thin rope and secured them tightly. He made me get on my knees and tied the two ends of the rope to the heels of my shoes. The rope was tight and my balls were stretched away from my body. They were one mass of hard flesh and turning purple.

He put weight on the chain of my nipple clamps and makes me crawl across the floor and then crawl back to him. I let out low moans as each knee forward pulled the rope tighter, tugging harder on my balls.

My nipples were burning as the weight swung and tugged my nipples. Henry just laughed and told me to come suck his cock some more. This was my kind of guy.

As I crawled to him sitting on the couch, his cock was standing upright, hard as steel. He told me to crawl faster and I saw a leather riding crop in his hand. My mouth reached out for his cock and licked his pole shamelessly.

Then I felt the sting of the crop land directly on my tight mass of nut meat. Then another smack every few seconds as I licked his balls. I groaned with pleasure and he alternated between smacking each cheek and my bound balls.

I then managed to get his cock in my mouth and deepthroated it again. He held my head there for a few seconds.

He switched back to the leather paddle. The nipple weights were swinging as my mouth bobbed up and down on his stiff cock. He then bent down and we kissed passionately.

He stood up and told me to crawl to the bedroom. As I began the slow crawl, Henry cracked my balls with the paddle. He pulled off his leather belt and swung. He connected with both cheeks and balls with one blow.

He bent down and rubbed my red cheeks where small welts from the belt were forming. He squeezed my balls and whispered in my ear that he was going to stick his hard cock into my slutty pussy when we got into bed.

Meanwhile, my buttplug was still vibrating away.

Once in the bedroom, Henry pulled down my panties and removed the buttplug, got behind me and rubbed his hard cock over my balls and pussy. His cock was so hot and hard that I begged him to fuck me right now.

He just chuckled and proceeded to stick his mushroom head in my hot hole. He pulled out and stuck it back in as I felt his cock sliding over my tight balls. He was teasing me!

Then he put his cock in my mouth and made me suck. At the same time, he untied the rope from my heels.

I stood and as I am attempting to get into bed, he grabbed the end of the rope and pulled. This stopped my momentum and tugged my nuts unmercifully. He laughed, dropped the rope and got in bed with me.

I laid on top of him and we kissed again. He spread my cheeks as we were kissing and stuck one finger, then two fingers in my pussy. I was primed and ready to receive his 8 1/2" of hard meat.

I grabbed his rigid cock and pointed it towards my quivering open pussy hole. Panties were around my knees. I touched his mushroom head to my pussy lips, then pulled it back and placed it inside my butt cheeks and rubbed his hard cock up and down my crack.

The heat from his cock had my pussy hole gaping open and spasming!

My slippery pussy lips glided up and down his shaft from the outside. I anticipated that the moment of getting penetrated would happen soon and had me panting and moaning. We continued our passionate kissing.

Henry then grabbed his cock and pulled it away from my cheeks leaving me humping air while our lips were still locked.

He grabbed my hips and pushed me off him. He then told me, "You slut, it is not time for you to feel my hard cock buried inside of you. You have not earned that yet. You will suck my dick until I splatter my sperm and cum on your face. You can taste what drips off, but I want most of it to dry on your face.”

He had to see the disappointment in my eyes for not having been fucked, but excitement for his plan quickly overtook me. My face would soon have a baptism of jism!

He placed my inflatable buttplug in my pussy and pumped it up until I was moaning from the pressure. He retied the ropes to my heels. He added another rope and tied my hands behind my back and attached it to the rope around my balls.

He made me wiggle off the bed and onto my knees to the floor. Every movement tightened around my balls and was painful. He was enjoying this. So was I.

My balls were pulled outward away from my body and looked like they could be part of my ass. He leaned over behind me, his hard cock and large balls laying on my shoulder and tugged on the ropes causing painful pleasure and laughed at the moans.

He commanded, "Now sissy, back out to the couch to suck my cock.” I slowly turned on my knees, facing the door and saw his hard cock in my face. He said, "open wide" and proceeded to let me suck him for a few seconds before pulling out.

He replaced his cock in my mouth with a penis shaped gag instead of a ball gag. This muffled the moans. He grabbed the crop and commanded me to move. The crop smacked my tortured balls and I proceeded out the bedroom door to the couch.

On the slow knee march to the couch, Henry alternated smacks between each asscheek and balls. In the bedroom, he had also tied a rope from the head of my hardening clit to the hanging, weighted chain of the nipple clamps.

A few times, he pulled the rope as I was moving forward and the abrupt stop caused my balls to burn and the weights and clamps to swing. My sensitive nipples were searing. He just chuckled and said that I was becoming a good cock slave.

Henry stood in front of the couch and asked, "Are you ready for some cockmeat to feed on"? I looked up at him and shook my head and say yes through the gag.

He removed the cock gag and I said, "Please master Henry, I need to feel your hard cock deep in my throat. I need your hot cum to explode on my face and will eat only the cum you allow me to eat.”

He grabbed the back of my head and shoved his cock down my throat. My gag reflex had been trained and he was completely in. My tongue licked his nutsack. He moaned and left it buried for a minute. All the while, my throat and jaw muscles were massaging his organ with passion.

He then began the face fuck again. He felt the urge, but pulled out, grabbed the paddle and cracked my cheeks and nuts. His hard, slimy cock was bouncing in front of my mouth. I managed to get the head and sucked it.

With the other hand, he tugged on the nipple chain. I was writhing in ecstasy and he was not far behind.

Henry couldn't believe sex could be this erotic, kinky and fun!

He sat down and I begin bobbing up and down on his hard cock. Each movement of my head, up and down, tugged on my nipples and squeezed my nuts.

He reached over and lifted my arms, causing my nuts to turn to fire. We were both in constant moan manner. I knew he couldn't last much longer.

He released the rope from my hands, my balls dropped but were still attached to the heels. I began rubbing his balls with one hand and massaging his chest with the other. No hands stroked his cock, only mouth and throat.

He began to feel the bubbling urge.

As his long fat cock slid in and out of my throat, he told me between panting, "You cocksucking bitch, I'm about to cover your face in a puddle of cum". This made me suck even harder.

He stood up and his cock popped out of my mouth. I asked him to let me jerk his load onto my face, but he wanted to direct the load and told me that I could do it next time.

He grabbed his veiny, throbbing, slippery cock with his right hand and placed my head in position with his left. "Don't move bitch,” he commanded.

He began slowly stroking his steel pole and grabbed the nipple chain with his left. He lifted and dropped the nipple chain as he rubbed his cock.

The weights tugged on my tender nipples. He then decided just to hold and tug the chain.

My mouth was wide open hoping to catch whatever sperm he would shoot in. He was stroking faster now, his knees buckling, his heavy nutsack contracting. I rubbed his legs, muscles tensed.

We were both moaning. Then you shouted, "Here it cums bitch and don't swallow it"!

His first spurt was a string of hot, white goo that hit the bridge of my nose and left a trail across my mouth and onto my chin. He aimed the next thicker wad directly in my mouth.

The blast was so powerful as I felt it hit my tongue. This spurt was thick and laid on my tongue.

The next three spurts hit my right cheekbone, eye and forehead. There was so much stringy, thick cum that the right side of my was almost covered in jism. I laid my head back so the heavy spurts wouldn't roll off.

Henry aimed the next four spurts on the left side of my face. The first went up my nostril and the next three plastered my face. The two final shots of cum were in my mouth.

I could taste the nostril shot as it slipped down the back of my throat. He saw the thick load on my tongue and laughed.

Then he stuck his still rigid cock in my mouth and told me, "Yes, cocksucker slut, you can swallow now.” I worked his cock over and sucked every drop out.

Then I rubbed his cock all over my face and picked up whatever cum stuck and licked it off. I got to eat the majority of it and a thin film of cum covered my entire face and would be dried soon.

I continued licking until he was soft. I did so well that he released the air from the buttplug. I fell into his arms and we hugged and kissed for some time.

To be continued as Story 3.

Story URL: