An Unexpected Encounter with a Contractor
Contractor — I put up an add for some CNC play. I received a reply from a younger bi guy. I gave him the address as I was the only one home. I answered the door. A guy with a dad bod at the
A Curious Encounter with the Neighbor Girl
Other Neighbor Girl — I go over to her house to find her reading her dad’s Penthouse Letters. I asked her if any stories stuck out. She says, “One. This guy took home a tranny
An Unexpected Visit to My Ex's Mom
Ex Girlfriend’s Mom — Family around the corner that I’ve known since 6th grade. We were all school and after school friends. I hadn’t stopped by in a while. Now a junior in
An Unexpected Visit Before Christmas
Big Samoan, little surprise—. Several years ago I answered a local CL ad looking to get sucked. He was close and hosting, so I went over to his place. It was close to Christmas and he had all
A Unique Bond: Chemistry Tutor and Student
Chemistry tutor — back in 87, our neighbor decided to get her GED and go to nursing school. She was having trouble with Chemistry and my mom graciously offered my services. Over the next
Unexpected Connection in the Shower
Trans Singer in my brother’s band Part 4 — Sally looks at me and says, “Let’s clean up and go to bed.” I take another swig of Ouzo and agree. We go into the master and
A Late Night Conversation on the Back Porch
Trans Singer in my brother’s band Part 3. She starts to rock back and forth, my cock buried inside of her. Slowly as she kept kissing me, then a little faster. Faster now, she was leaning
A Birthday Surprise with Unexpected Company
Trans Singer in my brother’s band Part 2 — “Seriously. Come in.” She repeated. I said, “OK, but just for a minute.” I popped the tape out of the deck, parked
Fun Times in the Band's Recording Studio
Trans Singer in my brother’s band—
My brother had a band back in the 80’s and they did well. Sally would come over to write or record. I ran the board and Sally would nail the
Unexpected Lunch Meeting in the Van
I met a buddy for lunch about a week ago. We were standing by his van and he said, Check out what I have in the back.” He opened the side door and I got in. He got in behind me and shut the
An Unexpected Encounter with the Neighbor
This happened when I was much younger. I was called by the next door neighbor who needed a hand working the winch to get his motor in his Mustang. I helped him, he secured the motor and said,
An Unexpected Encounter During My Collection Route
I was much younger, working as a collector for the newspaper. I was given my daily stops, 6 if I recall, and I was on my way. I drove to the first stop and an older man answered the door. He was
Unexpected Encounters at a TS/CD Meetup
I was at a TS/CD meetup party on a Saturday afternoon. I was sitting on a couch talking to a couple of guys, when this obvious Domme put her foot on the guy next to me right on his leg and said,
An Unexpected Visit to a Big Guy's Place
I responded to a posting for a guy with a small cock. He emailed back with the address when I let him know that I swallow. I pull up, get out. He meets me at the door. Big Samoan guy. I figured
Unexpected Encounter in a Parking Lot
I responded to an ad looking for a bj. We did a back and forth and finally decided to meet in a parking lot. I drove over and parked by his work truck. He opened the side door and motioned for me
Unexpected Meeting at the Construction Site
I posted an ad in hopes of finding someone that needed to cum. A construction guy replied, and after a few emails I was driving to his site. He told me to park and meet him on the second floor. I
Unexpected Connections in Urban Settings
In guys for guys, I post an ad every time I get the itch to suck, and without fail, the same bitter gay troll emails back to me, “FAKE POS” and this baffles me, because a lot of older
