Pizza Delivery Story

I was 20 years old, and it was the summer after my junior year of college. I was home for the summer, and looking to make a little money during my last real taste of "freedom" before entering the real world. There weren't a lot of place hiring, but I managed to get a part-time job delivering pizzas for a local pizza place. It wasn't perfect, but it let me make some money while allowing me plenty of free time to spend with my friends and my girlfriend.

I had been with my girlfriend, Hannah, since my freshman year of college, and she was great. Athletic, tight body, pert, C-cup breasts, and just oozed sexiness. Throw in that she was smart and funny, and her family loved me, and things were practically perfect. The only downside was that she wanted to save herself for marriage. So whenever we started to get hot and heavy, she'd stop us short, and I'd be driving home with blue balls. More than one time I couldn't help myself and I would stop in a secluded area to relieve myself.

This frustration, for a young man in his sexual prime, is far from ideal. But I loved Hannah, and we had everything planned out for our future, so I wasn't really looking for an "out". But while I was working one night in early July, another option was put in front of me.

It was a Friday night, which meant I was going to be really busy. Normally this would have been fantastic, but I had pulled a muscle in my back the night before at softball, and I was not moving very well. Money is money, though, and I was pushing through the hot, Des Moines night.

At a little after 9pm, my boss tells me I had a delivery to the nice part of town. This area was full of mansions, the kind that had guest houses the size of middle class homes. Depending on who ordered, you could expect either to get stiffed on a tip because they didn't care, or you'd get a huge tip because money didn't mean anything to them.

I take the order (4 large pizzas and 3 sides of garlic bread) and drove the few miles down the road to the guardhouse that you have to go through to enter the rich neighborhood. The guard chuckled to himself when I told him which house it was, telling me that the son was having a pool party out back, and to bypass the front door and go directly around to the pool.

I pulled up to the house and saw 5 or 6 cars in the long driveway. I did as the guard said and walked around the right side of the house to the backyard where the pool was. As a came around the corner, I was shocked to see 4 muscular guys and 3 gorgeous women around my age, all completely naked!

I stopped in my tracks and just stood there for a second gathering myself. After a moment, I cleared my throat and said, "PIZZA!" Everyone looked over, and one of the guys jumped out of the pool to come over. As he was walking over, I couldn't help but notice the impressive size of his cock and balls. While soft, they swung long and low. I caught myself after a second and looked up at his face, and he laughed.

"Hey man, I'm Bobby. Thanks for the grub!" he said.

"Uh, hi! The total is, uh, $62.37," I replied, while fumbling with the food.

Bobby stood there smiling as I kept struggling to get the food out of the warmer.

I finally got the food out of the warmer and asked Bobby where I should put it.

"Bring it over to poolside. It's too hot to not take advantage of the water," Bobby said, leading me toward the pool and the other people.

Everyone smiled and waved, telling me thank you for bringing the food. I just stood there smiling and trying to subtly look them up and down for jerk material later that night.

Bobby came back from the house with a $100 bill and gave it to me, telling me to keep the change. He then followed me over to the fence, making small talk. Before I had a chance to open the gate, he asked, "Hey man, you want to come back over after your shift? Those 6 are all couples, so it kinda sucks being the 7th wheel, haha."

I laughed, and stuttered out, "I'd like to, but I'm not sure I'd be able to stay around here long without having a problem, if you know what I mean." I gestured down toward my waist, laughing.

Bobby smiled, and I noticed him looking at my groin a little longer than I expected. I also noticed his cock twitch just a little as he looked at me.

"Haha, you'd be surprised how relaxed things are. I think you'd be fine, and I doubt anyone would be offended if you got hard looking at them. Their egos would love it, haha," Bobby told me.

I laughed and told Bobby I would think about it. Bobby wrote down his phone number on the receipt and handed it to me, "Call me if you are heading over so I can let the guard know. Hope to see you later!"

I went back to work, but naturally I couldn't stop thinking about what I would do once I got off work. Hannah texted me that she wasn't feeling well so she didn't want to hangout that night, so my excuse for being busy was thrown out the window.

My horny thoughts got the better of me, and I texted Bobby telling him that I would come over once I got off work at 11. He texted back that he was glad to hear that, and that the guard would let me through when I got there.

I clocked out after a good night of work, and drove over to Bobby's. The guard smiled at me as I drove through the gate, and I pulled up to the house. I sat there for a second, forcing myself to get out of the car and walk around the side of the house.

I opened the gate and said hi to everyone, and Bobby jumped out of the pool again to greet me. Once again, I couldn't help but notice his huge cock and balls. It had to be 7" long and was thick, and it was still completely soft.

I had always considered myself completely straight, and had never even really thought about doing anything with a guy, but I'd be lying if I said I didn't notice a really nice cock when I would watch porn. Every now and then I'd think about what it would be like to hold a hard, throbbing cock in my hand.

Bobby introduced everyone to me, and told me I could leave my clothes anywhere. I swallowed, and walked over to a chair and slowly got undressed. Everyone went back to chatting in the pool, while Bobby asked everyone if they wanted to get in the Jacuzzi with him. They declined, but he went over and got in the Jacuzzi anyway.

I finally stripped naked, and decided joining Bobby in the Jacuzzi would be the easiest way to get used to being naked around everyone. Bobby watched me as I walked over to the Jacuzzi and climbed in. As I slid down into the water, I couldn't help but moan as it hit my sore back. I told Bobby about it, and we chatted for awhile.

A little after midnight, the other 6 decided to call it a night and left. Bobby and I discovered we had a lot in common, talking about sports, girls, and college. Eventually, the conversation turned to how frustrated I was sexually, and he told me that his girlfriend lived in Florida, so he had to take things into his own hands too.

I asked him what he did to deal with that kind of thing, beyond just jerking off. He paused for a second before telling me that he actually jerked off with some of his friends, and that the thrill made it even better.

My cock jumped a little underneath the water, and I told him that I had never done that. He smiled and asked if I wanted to. I thought for a second and decided that it might be fun. I told him that my back was really bothering me though, so I didn't know if I wanted to get out of the Jacuzzi.

Bobby responded by saying that he had a massage table in the house and that he had experience massaging his girlfriend when she was in town. He then asked if I would be comfortable with him giving me a massage.

I thought about it for a second. A naked man, one that had a really nice cock, was offering to give me a massage. My cock jumped under the water at the idea. I had to admit that the idea sounded hot, and hey, my back did need something to help it feel better. I told Bobby that I thought a massage would feel great.

We got out of the Jacuzzi to dry off, and I couldn't help but notice that his cock was even longer and thicker than before, but still hung low. My cock just kept jumping the more I looked at it or thought about it.

Bobby and I headed inside and he set up the massage table while I grabbed a couple beers from the fridge. By the time I got back to the room, Bobby had everything set up and I laid down face down on the table with my hands by my side.

Bobby took some oil and dripped it on my back, then slowly but firmly pressed down on my shoulders and back. His hands felt great on the sore muscles, and the more he massaged, the more I relaxed and just enjoyed it. For a moment, I forgot that we were naked and I just melted into the table.

After a few minutes, he moved down to my lower back, and I felt something warm brush past my hand. He kept massaging, asking how it felt and making sure I was enjoying it. I assured him that it felt great.

Bobby then asked if I wanted him to massage my legs and/or ass too. I hesitated for a second, but I felt comfortable with him so I said sure. Bobby shuffled lower along the table and I felt something warm brush past my hand again. I moved my hand slightly so it hung over the edge of the table.

Bobby continued to massage my legs, moving up from my calves to my hamstrings, and eventually up to my ass. It felt fantastic, and I told him he should do this professionally. He laughed and said he didn't mind having the practice.

As he continued pressing on my buttock, the warm presence brushed my hand again, and I instinctively brushed back. Bobby paused for a second, and then pushed his warm cock, still soft but huge, into my palm.

I wrapped my fingers around the shaft, barely able to get around the whole thing. I felt it throbbing; the veins pushing under the skins; and slowly moved my hand up and down the shaft.

Bobby moaned, saying that it had been months since his girlfriend had been around and that my hand felt way better than his own did on his cock. It showed, since he had become completely hard, and had to be 10" long and as thick as my wrist.

I rolled over and my rock hard cock popped out from under me. Bobby took it in his hands and massaged it just like he had done with the rest of me. It felt fantastic.

We looked at each other and laughed at how the night had become what we didn't expect it to. I sat up and suggested we put some porn on the tv. We walked over and sat down on the couch next to each other, reaching over to stroke each other's hard cocks.

I honestly can't remember what porn was on the tv, because my attention was on the huge dick that was in my hand. I knew that I wasn't going to last very long, but Bobby spoke up that he was close to cumming right before I was going to say it.

I quickened my strokes and Bobby did the same, and within seconds both of our balls jumped and huge streams of cum came shooting out of our cocks. Stream after stream, until our torsos were covered with it.

We sat there for a few seconds, breathing hard, then Bobby said that I was welcome to come over any time. I responded that I anticipated coming over quite often.

I grabbed my phone and I had missed a text from Hannah. She was feeling better and wanted me to come over and watch a movie with her. Bobby and I got dressed, laughing about how quickly girls can change their minds. As I opened the gate and walked to the car, Bobby called after me, saying that he thought he would want more pizza the following night.

I laughed, and smiled to myself thinking how fun my summer had just become...