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privateer269

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All (20) TS / CD (17) Straight for Gay (2) Couples (1)
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A Unique New Year's Eve Anniversary Celebration
New Year's Eve anniversary 3. He was turned sideways on the sofa. Legs spread masterbating for me. I was watching and stroking my cock as well. I couldn't resist any longer. I went down on

Posted by a TS / CD

By privateer269

A New Year's Eve Transformation Celebration
New Year's Eve anniversary 2. I put some sexy bedroom heels on him. They are black slip on sandals with the feathery strap and 2 1/2 inch heels. His feet are bigger than mine, but it just makes

Posted by a TS / CD

By privateer269

A New Year's Eve Transformation Celebration
New Year's Eve anniversary 2. I put some sexy bedroom heels on him. They are black slip on sandals with the feathery strap and 2 1/2 inch heels. His feet are bigger than mine, but it just makes

Posted by a TS / CD

By privateer269

A Unique New Year's Eve Anniversary Makeover
New Year's Eve anniversary 2. I put some sexy bedroom heels on him. They are black slip on sandals with the feathery strap and 2 1/2 inch heels. His feet are bigger than mine, but it just makes

Posted by a TS / CD

By privateer269

Celebrating Our Anniversary with a Twist
Last night, New Year's Eve, was my boyfriend's and my anniversary. We have been together for a year now. I just recently posted about The Christmas Party, where my boyfriend made one of my

Posted by a TS / CD

By privateer269

A Christmas Party with Unexpected Twists
The Christmas party 2. We returned to the party. Me with no panties and an outfit so short my cock hung out of the bottom of my skirt. My boyfriend in his tuxedo with no shirt. He looked very sexy.

Posted by a TS / CD

By privateer269

A Festive Night of Unexpected Connections
The Christmas Party. I posted here about a year ago. My first time in public dressed up as a woman. I went to Fantasy Fest in Key West. I then went out in Fort Lauderdale New Years Eve. I met a guy

Posted by a TS / CD

By privateer269

A Relaxing Evening at the Lake House
Tom's woodworking installation part 2. We had settled up. I had cleaned up the job and loaded up my tools. I was ready to go. Tom asked me if I wanted a beer or cold drink before I left. I was

Posted by a straight man

By privateer269

Weekend Project at the Lakefront House
I have always been a straight man. I am in my fifties and divorced. I run a high end woodworking company. We build custom bars and cabinetry. I have worked for a client on a number of commercial

Posted by a straight man

By privateer269

An Evening of Unexpected Roles and Fantasies
Part 2. I laid back on the bed and he went down on me. He had me up in no time. I told him, it's time. On your knees to serve your mistress. He was kneeling and ready. I ran my cock in the

Posted by a TS / CD

By privateer269

A New Year's Eve Connection in Fort Lauderdale
I had posted back in January that I went out on New Years Eve, in the Wilton Manors area in Fort Lauderdale. I went in full dress, as a woman. I met a man there that night. It turned out we live

Posted by a TS / CD

By privateer269

A New Year's Eve Date Night Adventure
I posted about my New Year's Eve 3. I could enjoy the feeling of his cock moving inside me. The in and out. The feeling when he is bouncing against the sphincter and knowing that he is really

Posted by a TS / CD

By privateer269

A New Year's Eve Encounter in Fort Lauderdale
I posted my New Year's Eve in Fort Lauderdale 2. He came in my mouth. Like the first time, it was a huge load. I don't have a lot to compare it to, but he cums like a horse. It's more

Posted by a TS / CD

By privateer269

A New Year's Eve Encounter in Fort Lauderdale
I posted my New Year's Eve in Fort Lauderdale. I went out for a wild one night of play. I met a man who, as it turned out lives near me. We decided to see each other again and made a date for a

Posted by a TS / CD

By privateer269

A New Year's Eve Encounter in Wilton Manors
New Year's Eve in Fort Lauderdale's Wilton Manors area. Part 3 He gave me a long deep French kiss. I was really turned on and he was up and ready for round two. I told him that I had only

Posted by a TS / CD

By privateer269

A New Year's Eve Encounter in Fort Lauderdale
New Year's Eve in Fort Lauderdale's Wilton Manors. Part 2. I had spread my skirt to show even more and told him, well then you have to help keep me warm. He put his hand on my knee and

Posted by a TS / CD

By privateer269

Celebrating New Year's Eve in Wilton Manors
New Year's Eve in Fort Lauderdale's Wilton Manors area. For those who don't know, The Wilton Manors area in Fort Lauderdale has a lot of gay bars, dance clubs, drag shows and

Posted by a TS / CD

By privateer269

A Night of Flirting at the Hotel Bar
Thought I would share about days not that long ago. I had a girlfriend that was cute, sexy and liked the lifestyle. I would have stayed with her, but rich ex-husband came back, she went back. What

Posted by a couple

By privateer269

A Chance Meeting in Key West Hotel
Key West part 2 He asked me where I was staying. I pointed at the hotel right there. I was almost there when he stopped me. He said, so am I. I will walk you there. We walked to my door and he kissed

Posted by a TS / CD

By privateer269

A Journey of Self-Discovery at Fantasy Fest
Fantasy Festival in Key West is known for a wild time. A very decadent crowd, to say the least lol. I have been a closet CD for years. No one had ever seen me in dress. I have lingerie, sexy outfits,

Posted by a TS / CD

By privateer269