Author's note: Mostly true, the situation changed a bit to spice things up. While I didn't sleep with "Kathy's" mom (not for lack of desire, she was hotter than "Kathy"!), the motel event did actually happen.
Enjoy!
*
It was the early 1990's and I was 33, stationed in Savannah, Georgia. I'd been there for about four months and got a part-time job delivering pizzas, figuring that the extra cash would help and the time spent working would keep me out of the bars and out of trouble.
Kathy, my new girlfriend, worked there also. She worked at the same pizza store and we'd been dating for two months. Kathy was a 24 year old short little hottie with huge boobs, but not especially pretty. What she lacked in looks, though, she more than made up in body and personality. It was always great to hang out with her. We were about to take the next step in our relationship, meeting her parents, the next day. I hoped that hurdle was the last before I got into her pants.
It was a Thursday night, and the following day was a training holiday (ie, day off for you non-military types), so I volunteered to work the closing shift. It was about three minutes to closing and I had already cashed out when the phone rang. I gave Gary, the manager, a disgruntled look as he reached for the phone to take the order.
"C'mon, man," I pleaded, "you can ignore it this one time. I'm ready to go home."
Gary gave me a stern look and picked up the phone. "Thank you for calling [big pizza chain with mafioso overtones], may I take your order?"
I saw him jot down the order (yeah, no computers then) and I started making the pizza even before he hung up. After he did, I glanced up at the clock: 11:02 PM.
"You realize that I'm off, right?" I said.
"Just pay for the order with your tips and go home after the delivery," he replied. "If they stiff you, I'll reimburse you tomorrow."
I checked the address. It was in "The Hood" as we called it. There were several places in Savannah that a pizza guy, especially a skinny white one like me, had to keep his head on a swivel or else someone would liberate all his cash, accompanied by bruises or some cuts. We'd had two drivers robbed in the last six months and normally Leon, a massively-built black guy that nobody messed with, delivered to this area. The irony was that for all his mean looks, Leon was probably the nicest guy anyone would ever have the pleasure of meeting. Unfortunately for me, he was off that night to study for finals at the college he was attending. I was going to have to make the delivery.
Twenty minutes later, I nervously walked up with the small cheese pizza and twenty-ounce coke in hand. The delivery address was a sleazy motel that I'd never delivered to before. I knocked on the door to room 3 and waited. It was on the ground floor and I was angled so that if the door opened and I saw a knife or a gun, I could drop the food and make a break for it.
When the door opened, I was more surprised than if there HAD been a knife or gun sticking in my face. The woman that answered the door was probably in her mid to late 50's with salt-and-pepper hair cut into a bob. I could see that life hadn't been kind to her, and her face showed years of hard living. She was a few inches shorter than me and a bit on the thin side. The truly surprising part was that she was wearing a full-length nightgown that was completely see-through.
Her tits were small and kind of flabby, and she had the "old lady pooch" of a belly. Other than that, however, she wasn't too bad to look at. She had nice legs.
"Uh....pizza!" I stammered, averting my stare and looking past her and into the motel room instead. I noticed that there wasn't a single light on in there.
She turned and walked to the back of the motel room, leaving the door wide open. With her back to me, I noticed that she had a really nice ass. She pulled some cash from her purse, then turned around and stood there as if she wanted me to come into the room.
I'm a Star Wars geek. I wasn't surprised to hear Admiral Ackbar's voice saying "It's a trap!" in the back of my mind, so I wasn't planning on walking into that room. I shoved the pizza box out in front of me and repeated, "Pizza."
She gave me an exasperated look and simply stuck her hand with the money out. I glanced around the dark room and didn't see anyone, so I gathered up my courage and walked into the room over to her. I took the cash and set the pizza and soda down on the desk next to her purse. I thanked her as I started to walk out, but I made the mistake of looking into her eyes.
The second my eyes met hers, I knew I was going to fuck her. I could see it in her eyes...pleading, yet triumphant. The sexual connection between us was such a shock that I stumbled and almost fell. As I regained my composure, she had walked over and closed the door. It was almost pitch black, the only light coming around the edges of the curtain from the streetlights outside.
My breathing was rapid as she walked up to me, then I felt her slowly dropped to her knees in front of me. Nimble fingers unbuckled my pants, unzipped my jeans, and fished my half-hard dick out of my pants. The sensation of her wet, soft lips sliding down the head of my dick was exquisite. I'm sure that the situation heightened my senses...the dark, the mysterious woman, and all that, but she had the best mouth that ever covered my dick.
I felt the head of my cock nudge against the back of her throat, then her mouth slowly slide off it. Her tongue ran itself around my cockhead before the whole length disappeared back into her talented mouth. One of her hands caressed my balls while the other ran itself up and down my belly under my shirt.
She was mewling softly as she hungrily sucked my dick faster and harder. I knew it t wouldn't be long before my dick would explode in her mouth, and I told her, "Jesus, lady, you're going to make me cum!"
She yanked her mouth off of me. "No!" she said in a loud whisper. "I need to get fucked hard." She stood up, and in the dim light I saw her turn around, bend over the bed, and gathered her nightgown up around her hips. "Fuck me in the ass!" she commanded.
I was definitely wet enough from her mouth. I moved behind her, lined up my dick with her asshole, and slowly started pushing myself into her.
She obviously didn't want gentle. She slammed her ass back into me and my cock slid smoothly deep into her ass. I heard her gasp in pain, but she didn't pull away.
I immediately started to pump my cock in and out of her, but she hissed "Wait....wait..." It was difficult to keep from moving, to keep from twitching my hips and making my throbbing cock move inside her hot, tight ass. I was just about to give up and start fucking her hard when I felt her relax around my cock and heard her say, "Fuck me hard, honey."
My hands grabbed her hips and I started pounding into her with abandon. With every thrust, she grunted in pain/pleasure. My thighs slapped loudly against the back of hers. I felt her hand brush across mine as it shoved it's way beneath her, her fingers search for and finding her clit. She stroked it madly as I frantically fucked her.
"Unnngh....oh.....OH........YESSSSSSSS," she moaned. I could feel her asshole convulse around my pistoning cock as her fingers brought her over the edge to orgasm. It brought me to the brink.
