Trespassers will be Spanked (Letter)

Lover,

You wouldn't believe what happened to me last week, down by the old lumber mill a few blocks from where I work. It was a regular day at first, but somehow things ended up going terribly wrong...

I'd just gotten done with my lunch shift at the diner. When I went out to start my car, the engine was totally dead. I called my brother and he wasn't available to help me out until the next day, and since I'm only a few miles out, I decided I could walk home and cut through the back way.

The back of the mill was fenced off, and I admit, there might have been a 'No Trespassing' sign. Nobody was around, though, and the gate was hanging open. So I went through.

About halfway across the property, I heard some shouting. I turned and saw that someone was running towards me. As he got closer, I could hear that he was saying, “What are you doing back here?”

I was absolutely stunned. I decided I could play dumb, unbutton the top button of my blouse, and pray he didn't make too much of a fuss.

“I'm sorry, sir,” I stammered. “I was just passing through on my way home, am I not supposed to be here?”

He was a few years older than me, but still pretty young. He had a work shirt on, smudged with dirt, and the beginnings of a beard. His eyes told me that he didn't buy my story for a second.

“There's a dozen signs that say not to trespass here,” He said, pointing.

“I'm sorry-”

“I've got half a mind to call the police and have you arrested. I'm sick and tired of kids running through here and fucking with my equipment.”

He sounded stone serious. And I'm barely making ends meet working at the diner, there's no way I could afford any kind of altercation with the law. I was willing to do just about anything to make this problem go away.

“Please don't do that,” I said. “I really was just on my way home from work. See? Here's my name tag, I work down at Lucy's. Definitely not touching anything that isn't mine.”

He still didn't seem very amused. “Yeah, I'd recognize the uniform anywhere. Black mini skirt, white blouse...Lucy's got the best looking waitresses in town. But that certainly doesn't give you any excuse to barge onto land that doesn't belong to you. Now, I personally know the Sheriff...”
By now, he was digging around in his pocket for a cell phone, and I could practically see the jail cell that was waiting for me.

“Wait!” I begged. “Please don't call the police. There must be something I can do?”

This actually made him stop and think, which was a huge relief. Then he got a smile on his face, and he said, “Alright, fine. Follow me.”

I did, and he led me towards the back rooms of the lumber mill. It's actually kind of nice in there. They have a few offices, and he took me into what must have been his. It was pretty bare- nothing but a desk with a computer, and a few chairs.

“You want to know what has to happen to make it so that I don't call the cops?” He asked as he closed the door behind us. Suddenly, I started to feel a little uncomfortable.

“I do.”

“Well, trespassing can't just go unpunished. So you get to choose your punishment. I can call and get the police involved, or I can dole out my own idea of a consequence.”

I bit my lip. My mouth was now dry. “And...what would that be?”

He grinned. “A nice, hearty spanking.”

I felt my face and ears get hot. I must've been red as a tomato. “I'm really not comfortable with that...”

“Police it is, then.” He reached for the phone on his desk.

“Wait!” The room felt warm. I pulled my hair back to lift it off my neck. “Please don't call them. You can spank me, so long as I can go right home as soon as it's over.”

“Of course,” He agreed.

I shifted from side to side in discomfort. I couldn't believe I'd gotten myself into this mess. My heart was pounding and I thought I might die.

“So...what do I...” I didn't even know where to go from there.

“Bend over the desk,” He instructed, coming up behind me.

I groaned in protest, but did as he told. The desk was cold on my chest and face. I could actually feel my knees shaking a little as they held my ass up in the air.

He walked behind me, and I could feel his eyes on the curve of my rump. I anxiously twisted my hands in my hair, eager to get it over with.

“I'm going to lift your skirt,” He warned and brushed my leg. I wasn't going to have that, though.

“I'm really not comfortable-”
“It's this or the Sheriff.” He reminded me.

I chewed on my lip, then gave a resigned sigh. I couldn't afford it... “Go ahead.”

My black skirt was so tight, he had to wiggle it a little to get it over my round ass. I remembered that I'd put on my red lace panties that day, and shame burned deep in my stomach. He must have thought I was such a slut, wearing lingerie to work at a diner.

“Very nice,” He said. It was like he could see how humiliated I was, and wanted to rub it in. “Are these Victoria's Secret?” He grabbed the elastic waistband and snapped it against my skin. I jumped and squeezed my legs together. “Such a pretty little slut, don't you like that?”

I could feel a lump forming in my throat. I didn't want to cry. I didn't want to give him the satisfaction.

He grabbed at the waistband of my panties again, but this time, he pulled them down off my ass. I opened my mouth to protest, but I couldn't make any noise. The air was cold on my bare skin, and I could feel goosebumps erupting on the back of my neck. I tensed every muscle, just waiting for the moment...

He smacked me hard. The sound of skin slapping skin was loud in the quiet office, and I cried out from the sting of the blow. He moaned just loud enough for me to hear, and my stomach rolled that I was being used for him to get off.

“You going to trespass on my property again?” He bent down close to my ear.

“No,” My voice broke. A tear escaped the corner of my eye.

He spanked me again with his open hand, and I gasped. I could feel my body trembling from the impact.

“Sorry, I didn't quite catch that.”

“No!” I yelled, and he gave me another smack across the ass.

“Don't you give me attitude!” He scolded, and rained the spankings over my raw behind. I just clenched my teeth and let my tears of humiliation drip onto the surface of his desk. The force of his spankings pushed me forward, and my thighs dug into the edge of the wood. It stung like you wouldn't believe.

After what felt like forever, he pulled my panties back up over my tender ass and yanked my skirt back down. I got up and ran out of the office, my face red and streaked with tears. The rest of the way home was a walk of shame.

When I checked myself in the mirror later, my bottom was covered in red hand prints.

Honestly, though, love...there's really only one thing that's still bothering me about the whole thing.

When I remember everything that happened, with this stranger spanking me... When I think about it, it turns me on. I hate it, and the whole thing was just awful... But when I let my mind wander to how it felt, bent over that desk, I feel the wetness between my legs.

I know that my story is totally crazy, but I guess my point is...would it be okay if we tried that some time?

Lots of love, always,

Your Baby