My first meeting with Henry - Story 1

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.

I met Henry while drinking in a local bar after work in late August. (I was dressed in normal work clothes since I only crossdress on weekends.) We had some laughs and hit it off well. He was getting d***k so I offered him a ride home and he left his car. Went inside his house, he grabbed some beers and we sat on the sofa. He was too d***k to take off his boots so I offered to do that for him. He then staggered to the bathroom to take a piss.

He came back out to the sofa naked and sat back down. I acted as if this was not shocking to me. As I got to know him in the following weeks, he does such things for a reaction. Henry said this is how he relaxes and don't mind him. I saw his soft big uncut dick lying across his left leg and we laughed and talked more. He was in very decent shape and had been an athlete in college before dropping out to help his cousin in the construction business.

It was surreal to me since this guy was a man's man in looks and manners. A real amiable and good guy. He sat there naked as if this was normal and I went with the moment. My girlfriend was away and I was horny and becoming less inhibited as the alcohol took effect. I went to piss, came back out naked to reverse shock him. He laughed as he saw me knowing I was in tune with his actions.

I stopped behind the back of the couch, heart racing and playfully decided to rub his shoulders. He reaction was to close his eyes as the TV blared in the background. I then turned off the light next to the couch and lowered the volume of the TV. My hands could feel the muscle tone and tension in his shoulders. Then I moved my hands down his chest and noticed his cock starting to grow and twitch. His fat mushroom head was peeking out of the foreskin.

Moved my hands behind his back and continued to massage him as he sat there and I kept eyeing his cock. Then I teasingly moved my hands down to his stomach and caught his eye. As I was bent over the couch, I felt the chemistry and moment was right so I kissed him. He then opened his mouth and we tongued each other. He had never kissed a man before, but was a rather good and gentle kisser.

My hands kept getting closer to his hardening cock and could feel its heat. I grabbed his now throbbing cock and he kissed me with passion and moaned. I stroked him for a while, gentle teasing strokes while continued kissing.

I broke the kiss, climbed over the sofa and gently put my mouth on his big cock. He groaned and said he had not had head in months and he didn't care who was sucking his cock. His fat engorged cock barely fit the width of my mouth. I nibbled and licked his foreskin and pushed it back with my tongue. He had a nice swollen spongy mushroom head.

I attempted to deepthroat him slowly and sucked up and down his shaft. Could manage all but the last inch or so down my throat. I bobbed up and down with a steady, hungry, passionate pace. All the while, my hands were rubbing his large nuts and his strong legs.

Within 5 minutes his cock got larger in my mouth, his body tensed and I was tasting his hot cum in my mouth. I did my technique of pressing my tongue on the underside of his fat shaft and moving it forward with each spurt. This results in a more f***eful cum blast.

Spurt after spurt of tasty cum filled the back of my throat. No gagging tonight as I swallowed it all at once. I licked him clean, told him to get up and walked him into his bedroom and he flopped on the bed. I could now see his muscular ass and defined leg muscles. I pulled the covers up over him. He was fast asl**p.

I then got dressed and left. The next day, I thought what the hell did I do and wondered what he would think when he sobered up and how he would get his car.

Was hesitant to go back to the bar and face him, but the next Friday I went to the bar and was nervous. Spotted him and acted normal as if nothing had happened. He said he had a great time and I sucked him well. He asked if I would suck him again. It was such a relief to hear him say that and I agreed to be his cocksucker, but it must be discreet.

He stressed that he had no interest in sucking me and I said that was ok with me. We made a date for the next day in the afternoon. He told me he had some fun ideas and I told him that I would come dressed as a woman. Without missing a beat, he said to do it.

To be continued as Story 2.

100% (9/0)
Categories: BDSMFetishShemales
Posted by hotcdsub
2 years ago    Views: 846
Comments (5)
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6 months ago
if i were you, i would do same...and i'd be very ok with him not sucking me either. thanks for sharing.
2 years ago
Fantastic super erotic
2 years ago
2 years ago
great story!
2 years ago
great stuff, more please!