The Telemachus Story Archive

The Pizza Delivery Boy's Halloween
By Catglee (Illustrated by catglee)

The Pizza Delivery Boy's Halloween

by Catglee

Pete Devilyn is a Sophomore at Berkshire County Community College. The kids in school would tease him about his last name. They said he has the Devil in him. Maybe yes, maybe no, although he does have a “devil-may-care” attitude.


He works his way through school by delivering Pizza in the evening. He is only two weeks on the job this Halloween evening. He knows the town well enough so he finds the addresses real fast. The customers are friendly and are generous tippers.


His co-workers start teasing him about how this evening can be a threat to all Delivery Boys. They spin tales of Spooky Houses and Goblins, how Pizza Boys are captured and abused in dark rooms.

Pete laughs off such dire predictions as nothing more than a Halloween Prank.


A phone call comes in for an order of pizzas to be delivered in Pete's next round. When he is given the address, his co-workers warn him that that address is that really spooky house on the outskirts of town. Pete laughs it off and hops on his skateboard with several boxes of pizza. It doesn't take him long to find the address.


He walks up to the door and rings the doorbell. It is several minutes as he now nervously waits for someone to answer the door. As the front door opens, he doesn't hear someone coming up behind him.



Just as he hands off the boxes, he is grabbed from behind and forced through the door. Pete struggles to break free, but he is over-powered and forced inside. They take him down in the basement where there is a holding cell.

His clothes are removed, revealing a tight-muscled tattooed body. Pete has a nice-sized cock that pleases his captor. The red hat stays on.


Pete is taken to another room where he is strung up to the ceiling. He fears for what may come next. A little red whip stings his back. Much to his embarrassment, his cock gets hard with every crack of the whip. For the first time he realizes that this is an erotic sensation that goes straight to his prick.


His meaty nipples are then squeezed, twisted and pulled. This manipulation of his sensitive tits gets his stiff cock dripping with pre-cum. Another realization is: that when his meaty nipples are manipulated, the pleasurable sensation connects straight to his throbbing hard dick.


Taken to another room, another tormentor strings him up to a metal bar with his legs over his head. His hard cock and tight butt hole are fully exposed. He is slowly stroked up to a powerful ejaculation.

Through it all, the red hat stays firmly on his head.


Retied and repositioned, Pete suffers the indignity of having a greased-up dildo on a pole pump his tight butt. At first it is shoved slowly in and out. It nudges his prostate with every thrust. The pace is picked up, faster and faster, mercilessly ramming his tight hole until he shoots a big load on his tight abs..


Untied, stood up and hand-cuffed behind his back, Pete is butt fucked by the guy in the mask. His sphincter is sore from being plowed by the dildo on a pole, but Pete tolerates his ass being plowed without a whimper. The red hat keeps firmly in place on his head.


After the man in the mask has his way with Pizza Boy, he is turned over to another guy in another dark room. Strung up with his legs spread wide, his sore butt hole is fingered, his prostate is nudged while his once again erect cock is manipulated. It takes a while to get his prick to shoot another load, but his tormentor is persistent. After he is forced to shoot his third load, Pete is taken down and shoved into another room.


Just as a change of pace, Pizza Dude is soundly whipped across his broad back and firm buttock. Soon his back and butt glows a bright pink. The strokes are firm and punishing but not to the extent that they cause any real damage to the naked delivery boy. After the sound whipping, Pete is left there to catch his breath and composure. He never loses the red hat.


Devilyn is allowed a moment's rest to catch his breath. In the silence of the dark room he realizes he has lost all track of time. He wonders how else is he going to be played with?

For the next several hours he is rimmed, wanked and sucked off. So many sensations new to him have his head spinning.



One bizarre episode has him stretched out on a metal rack with lighted votive candles underneath. The warm sensation on his backside is erotic indeed! Another ejaculation is expertly coaxed out of him.


Next he is brought into a room that has the most god-awful couch cover he has ever seen.. It is even uglier than the one in his grandmother's house. He is tied sitting down, arms spread wide. Two other guys have their way with him while he leans back and tolerates their hands all over his naked body.


After they have done with him what they liked, they leave the room and his original captor comes up behind the couch. For the first time all evening someone speaks to him.


“We are all very impressed by the performance you delivered. You took everything like a man, not whimpering, not cry out, not whining. As a reward for your delivery, accept this token of our appreciation.”

Pete looks inside the envelope and sees $1,000 in 20's and 50's. Wow! His best tip ever!

The man in the mask continues: “Here are your clothes back in good condition. It still is Halloween and there is a party upstairs in the ballroom. It would be an honor if you join us. I ask you not to shower however, the guests will enjoy having you there smelling like a sweaty “hot fuck”.

The Pizza Delivery Boy accepts. At the party he looks aroud to see if he can identify the guys who played with him. The party goers are all in costumes and masks, He can't figure out who is who. Anyway Pete the Delivery Boy has an enjoyable time long into the early morning.


The next day his co-workers ask about last night's delivery. All that he admits to is that he was invited to stay for a very enjoyable Halloween celebration. “I guesss the Devil got into me a bit at that spooky house. Some wicked things happened for sure, but I had a Hell of a time.”