Pizza Delivery Dare

[wolf86]

This just happened last night... I'm writing this while my wife is still asleep. So my wife and I are staying at a hotel this evening on our way to see family for the long weekend. We got to the hotel about 9 and checked in and I convinced my wife to drink a bottle of wine with me. Well, one bottle turned into 3 and she got fairly trashed and I was feeling nicely drunk.

At this point my wife declares she is hungry and wants to order a pizza since neither one of us can drive at this point, and I agree because who doesn't love drunk pizza. So we look up a pizza place and try to decide what to order. Of course since she is drunk she is being difficult about deciding what toppings to get so I eventually dare her that if she will flash the delivery guy I will order whatever she wants and jokingly add that maybe we will get the pizza free. She laughs and says 'Yeah, right like some delivery guy is not gonna take any money just because he catches a peek at me'. Then I tell her 'no, probably not for just a brief look at you'. Apparently since she was drunk she took this the wrong way and said 'Oh so he won't think I am hot enough to give us a pizza for free? I bet I can at least get us a discount on something'.

Being drunk I immediately agreed before even asking her what she was going to do. Then I asked and she just laughed and said I would have to wait and see. So I called and ordered the pizza and again tried to get her to tell me what she was planning. She just gave me a devilish little grin and said I would see but I would have to hide so he wouldn't see me and mess up her plan. I was getting intrigued and horny because of the alcohol, and as time passed I started getting excited/anxious about some random guy possibly seeing her naked. I had no idea what she was actually going to do but I had a feeling it would be more than just a brief flash like I had originally thought.

As it got closer to time for the pizza, she had me get in the little closet beside the bathroom door which is on the left when you come into the room. It was one of those folding doors that had the little slats in it so I was actually going to be able to see out fairly well. She made me promise not to make noise or come out until he was gone so I agreed. After I was hidden, she walked out of view further into the room and I could hear her taking off clothes. I still didn't know exactly what she was going to do and all sorts of possibilities ran through my mind because my wife is not a shy person and has been naked in front of a few of my friends before. We even had a threesome with one of them after a night of drinking but that is another story.

Anyway, not long after I hear a loud knock on the door and a guy's voice say the name of the pizza place. My wife says, 'Just a minute I'll be right there'. She finally comes back into view and she is completely naked except for a towel around her hair. My heart starts pounding as she looks through the peephole and reaches for the door handle and I realize she is actually about to do it. But then she barely opens the door just enough for it to unlatch and jumps into the bathroom while telling him to come in and put the pizza on the bed and that her husband should have the money sitting the dresser. At this point I am a little confused because obviously I didn't leave any money laying out for him. Well the guy walks in kind of looking around and goes to set the pizza down. From what I can tell he is a slightly overweight guy probably late 20s/ early 30s.

After he sets the pizza down he just kind of stands there awkwardly for a minute looking for the money I guess. Then he calls out to my wife asking where the money is supposed to be, and she answers, 'My husband said he put it on the front corner of the dresser, it should be in plain sight'. He laughs and says, 'maybe I'm blind, I don't see it anywhere'. At this point she laughs kinda nervously and pokes her head out of the bathroom door to look at the dresser. His back is to her and he is looking around the room and saying something about maybe its somewhere else and I guess he doesn't notice her walk out of the bathroom completely naked right away. She gets about 6 feet away from him and asks if he has found it yet. He says no and turns to look at her and his eyes probably about popped out of his head as he kind of froze and just stood there stammering and stared up and down my wife's body. My heart is beating so loud at this point I feel like they will hear it and my cock starts to throb against my jeans. She laughs and says, 'Obviously you aren't blind like you said earlier', and he kind of turns away and apologizes. She then tells him, 'No its fine, I don't mind, you can look all you want'. He then mumbles something about her husband and she says, 'Don't worry about it he isn't here, this is what he gets for not leaving the money like he was supposed to'.

Then the guy laughs a little and tells her it will be $21.84 or something. My wife says ok and turns around and bends over to look through our bag. This gives him an unobstructed view of her ass and shaved pussy lips. I couldn't see his eyes real well but he had to be checking out her backside. Then my wife goes, 'Shit, he must have his wallet with him, hold on' and she stands back up unsteadily and turns to walk past him to her purse. As she tries to squeeze past him she sways drunkenly and bumps against the bed and sort of falls toward him. He instinctively goes to catch her and a hand lands on her rib cage right under her left boob. Apparently as she fell she let her hand bump into his crotch because she then made a comment about him being awfully excited for not having touched anything good yet. He stammered something and she laughed and then grabbed his hard on through his pants! I couldn't believe how excited/afraid I was watching her grab a stranger's junk! Then she said, 'Well since I touched you its only fair that I let you touch me and she grabbed his hand and put it on her right breast and slid it down her stomach to right above her landing strip.

She then told him, 'I don't think I have enough cash in my purse to cover the pizza and the tip so you can touch that if you want to accept that as part of your tip'. His eyes got real big and he slid his finger down to her slit and began rubbing her. She moaned a little and then he said something about this is awesome but I'm gonna need to go soon. My wife goes, 'Ok, let me get you the rest of your money' and looks in her purse. She tells him, 'I only have a couple $1 bills and a $100, can you make change for that?' and he says no he doesn't have enough cash for that. So my wife says, "You can wait for my husband to get here with cash if you want because I feel bad about only paying $2 for the pizza'. At this point I'm like what the fuck am I supposed to do now, I know this guy is gonna want more than $2 and she damn well better not give him the $100 after all this. But the guy says he really needs to get going and can't wait so don't worry about paying him. My wife asks him if he is sure, because she feels bad that the pizza will have to come out of his pocket.

Then, I couldn't believe it but the guy got some balls and told my wife that if it would help her not feel bad she could suck his dick. My wife then sat down on the bed and undid his pants and pulled his about 6 inch hard cock out and asked if it would be ok if she just gave him a hand job. He said oh yeah and she began stroking his dick. He only lasted maybe 20-30 pumps before he shot his load all over her tits and stomach. I can't really describe the feeling of watching a strange man pump several thick strands of cum all over your wife's naked body. He then pulled up his pants and thanked my wife profusely, saying don't worry about the money, that was the best handjob I've ever had, you are so fucking sexy. She laughed and said glad I could help and he grabbed his stuff and almost ran out of the room.

My wife then turns and lays back on the bed as I come out of my hiding place. I can see where his cum ran down her tits and stomach all the way down to her landing strip and thighs. She starts rubbing her pussy and breasts with his cum all over her. I immediately drop my pants and start jacking off over her naked body. I was so ready to explode that it only took about 20 seconds before I blew my load all over her pussy and stomach. When I did that she had a huge orgasm and moaned really loud then just laid there for a minute with her eyes closed. By this time we had both started to sober up, she kind of sat up and said, 'Holy shit did I really just do that?' and I told her that indeed she did and it was damn exciting. She then made a crack about I told you I could get us a discount and laughed. The rest of the night we ate cold pizza and fucked three times reliving her adventure with the pizza guy.

I would love to hear similar stories if anybody has them.

[piecenick]

We didn't go that far, but Delta caused us to miss a connecting flight so they put us up in a hotel one night. We didn't get there till about 1030pm, so all we could do for dinner was order pizza with the handful of meal vouchers they gave us. Whie we were waiting my wife went to take a shower, I walked across the parking lot to get a bottle of wine from a liquor store.

I didn't think I was gone very long, but when I got back to the room the pizza guy was there, my wife, who had just spent a week on French beaches topless, had lost all modesty, she was just in her panties. She had invited the young pizza guy is to join us, it was his pizza shop and his last order of the day. So we sat there, my topless wife sitting cross legged on the bed, while we ate pizza and drank a bottle of wine.

After the pizza, my wife told him she was exhausted from the long day of travel, he left, I was turned on from this but my wife was sleeping within 10 minutes.

[revani]

I was working as a chef for an Italian restaurant on a Greek island (what a combination) 8 years ago. It was a 6 month contract just for the touristic season. Money wise was good but owners wise was even better. We were the best team ever. A combination of Greeks and Italians in the same working environment.

Owners had set that rule. An hour before the end of a shift, all personnel where able to ask from the chef for a plate of food. They could take it away or eat it in a not busy corner of in the restaurant. My fav waitress was Elpida. A Greek short girl, beautiful face, short but really short hair and amazingly big boobs. She was the most polite girl that I ever met. She was the only one that was never asking for some food. During the second week after the opening I asked her why and I explained to her that there was no way to survive by the end of the summer like this. Even financially wise since that she had the opportunity by the management. She came back to me by saying that she didn't want to give me some more hard time before the end of the shifts. I said to her that it was also a part of my job. Also that I never met a 20yo girl with that way of thinking. I know, a bit cliche but true. I was 32.
She was also the funniest member.

By my reactions it was clear that I liked her and I think that by the time the same think happened by her side. There was that day though that she entered my kitchen and said to me that it was impossible for us to have something more since that we were working for more than 14 hours pd and only a day off pm. I just said to her that we had to figure out a way. I was so in love with Elpida. Then she made it clear to me that she had a boyfriend that was waiting for her after the end of the summer season.

The same day, it was something like 1am a windy night in the middle of May she entered my kitchen. She asked for pizza. I knew that she was vegetarian but I knew that this was also my chance. I took her order and as soon as she was about to leave my kitchen I offered her a glass of wine. I said to her that it we weren't busy and that she could wait next to me. Both of us we were tired but there was also something nice in the air. I had to make her laugh. I was preparing her pizza so I chose a really nice and massive bar of salami from my fridge. I never forgot that she was a vegetarian but I asked her how thin or thick I had to slice the salami. Her eyes became wide open and she was about to explode. She repeated to me that she was a vegeterian but she was looking also of the bar that I was holding somewhere between my legs. I said to her that she could be the piggy bank slot for the night. It was about time also to share our tips. She laughed hard I laughed hard and I lost my voice when she said me that she could get the ...real salami... after work.
We had a hell of a night with pizza wine and lots of sex. I cannot forget her boobs not even today. One of the best summers ever.

[wolf86]

This happened to one of the guys I shared a suite with in college. He delivered pizzas for a bit to get some extra money during the school year and worked most weekends. Anyway one weekend he happened to make a delivery to a friend of his then girlfriend and both of them answered the door naked, which he said surprised the hell out of him because he didn't know where that's where the friend lived or that his gf was hanging out with her that night. Both of these girls were pretty damn hot, his gf wasn't shy and a few times she stayed over with him in our suite I and a couple of the other guys saw her in her underwear walking around. He said if he hadn't needed the job he probably would have said screw it and stayed with them the rest of the night. As it was his gf gave him a quick blow job while her friend watched and played with herself. Of course he covered the cost of their order after that, which ordinarily would be fine except his gf knew he didn't have that kind of money to give away, but that's just the kind of person she was.

After writing this it just occurred to me that his gf and her friend had no way of knowing he would be the one to deliver their pizza since he worked for a large chain with a lot of delivery drivers. This makes me wonder if they had been planning to do this to any random guy who showed up, which wouldn't surprise me since she ended up cheating on him several times before they broke up. I know at the time we all just thought it was awesome but I wonder if he ever realized he maybe just got lucky?

[blusherlock]

While this doesn't involve any pizza, I think it goes best here.
I was staying at a local (non-chain) Miami hotel for a wedding. The first night, there were problems with the cable so I called down to the front desk. The only person working that night was an attractive Latina woman, probably in her mid 40s. When I called, she offered to come up and take a look at it. I had just gotten out of the shower and was pretty horny ( and didn't want to get arrested), so I put on a t shirt and a pair of cotton gym shorts... the flimsy kind that show every single bulge and movement.

I brought myself to erection after hanging up the phone, and had a big chubby by the time she arrived. With my heart pounding, I opened the door and let her in. I saw her eye catch sight of my cock through the shorts, and she didn't look away... but didn't say anything either.

As she turns to look at the cable box, I couldn't help myself but to pull out my cock and get in a few good strokes, just outside her peripheral vision. this made the bulge even more noticeable by the time she turned back to me. As she was finishing with the cable box, I whipped it out again while her back was turned. By the time she was walking back towards the door, I'm at full sail. I showed her out, and she gave me a good long look up and down before smiling and saying good night.

It was my first time "flashing" someone in such a personal setting, and it was a great thrill. Definitely set the pace for what turned out to be an amazing wedding weekend. Had a lot of fun with a couple of the bridesmaids ;-)