Top Definition
The act of receiving or giving oral sex to someone while riding a horse.
"how'd last night go with Kyndra?"

"Dude we went went horseback riding...totally got some trailhead"
by Spice Trader January 30, 2012

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giving head along the Oregon Trail to your partner as they ford the river.
You can only ride in my wagon if you give me trail head the whole way to Oregon.
by WB's January 12, 2008

The Urban Dictionary Mug

Lotsa space for your liquids.

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The Urban Dictionary Mug

Lotsa space for your liquids.

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The Urban Dictionary Mug

Your favorite word on a white mug.

Create a mug

The Urban Dictionary Mug

One side has the word, one side has the definition. Microwave and dishwasher safe. Lotsa space for your liquids.

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The Urban Dictionary T-Shirt

Soft and offensive. Just like you.

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The Urban Dictionary T-Shirt

Smooth, soft, slim fit American Apparel shirt. Custom printed. 100% fine jersey cotton, except for heather grey (90% cotton).

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Giving head to your partner along the Oregon Trail/ any trail you please (ski slopes included).
You can ride in my wagon as long as you give me trail head all the way to Oregon.
by WB's January 12, 2008

The Urban Dictionary Mug

Lotsa space for your liquids.

Buy the mug

The Urban Dictionary Mug

Lotsa space for your liquids.

Buy the mug

The Urban Dictionary Mug

Your favorite word on a white mug.

Create a mug

The Urban Dictionary Mug

One side has the word, one side has the definition. Microwave and dishwasher safe. Lotsa space for your liquids.

Buy the mug

The Urban Dictionary T-Shirt

Soft and offensive. Just like you.

Buy the t-shirt

The Urban Dictionary T-Shirt

Smooth, soft, slim fit American Apparel shirt. Custom printed. 100% fine jersey cotton, except for heather grey (90% cotton).

Buy the t-shirt