My Nude Day Pledge Disaster

"I'm slowly stroking myself."

"Oh, Bob. You're so special that I'll do what you asked and I'll try to let you keep looking at my pussy, too. But first, I need my finger slick. I'm sure it will hurt going in otherwise." I reached up from underneath and plunged my right middle finger into my cunt.

"Are you still stroking yourself?"

"Yes, Ruby. I think I'm close to ejaculating."

"Oh, Bob. Ejaculate is such a sterile word. I prefer to come; I come when I rub my clit, I come. Well, here goes. I'm a bit scared, I'm terrified it's going to hurt, but I'll do it for you, only for you." I took my finger out of my cunt and moved it around and behind my hip and, extending my middle finger, pointed it right to the crinkled edge of my asshole. "Is this the spot you want me to violate for the first time?"

"Yes, please do it, Ruby."

I lifted my hand away from my ass to extend my finger straight and have an angle I could plunge all the way in. I slowly pushed my finger to my first knuckle. "Oh, Bob, is this what you want? I feel so embarrassed, and it hurts. I'll keep going if you want, but I'd rather not."

"Push-in more, you promised, Ruby." He grabbed his cock and pumped, slow but hard.

I pushed in more slowly to the second knuckle. "I don't think I can go any further, Bob. It really hurts, and my finger gets bigger further down. I'd like to stop."

He was more grunting than speaking. "All the way in, Ruby. All the way."

I plunged it the rest of the way fast. "Oh, Bob. Thank you for making me do it. It feels so good. Oh, I never knew it would feel like this. It's wonderful." I rapidly pulled out and pushed into the hilt three times, and he exploded. He shot against the bottom of the pizza bag and got cum all over the floor, his shirt and pants.

I waited a minute for him to calm down and pulled my finger from my butt. "I think I heard you come, Bob. Did you?"

"Yes, Ruby. I came."

"I hope it felt as good as you hoped it would."

"Better, Ruby. Thank you."

"You're welcome, Bob. I'm feeling much better, and I'm still hungry. I'm going to stand straight up without looking back to you and walk up the stairs to get my card. You may use the towel to clean up if you wish. I'll come back down, pay and let you out. Don't be shocked when I come back down nude. You've already seen me intimately, and I'm too lazy to get dressed. Always remember, you may look but not touch. Do you understand, Bob?"

"I do understand, Ruby, and thank you."

"My pleasure and I'm getting up. Don't move until I've gone up around the corner."

I was stiff but rose and took each step deliberately. I tried to exaggerate the sway of my hips. At the middle landing, where the stairs double back 180 degrees, I could only see Bob's feet when I looked down to my left. I shifted my eyes up the staircase, and there saw Doug, sitting nude and erect on the top step. I put my finger to my mouth in a shush signal and kept stepping up the stairs. When I got near the top, I pushed Doug onto his back, squatted over his hard cock, and slowly lowered myself until he was fully engulfed by my sopping cunt.

We were well-practiced in a semi-tantric style and could fuck to climax with little movement and no sound. We both came in a couple of minutes, tensing up, planking, I think it's called, our legs over the stairs. I whispered, "I can't tell you how much I love you."

"I think you just did, beautifully." He whispered back.

"Where's my purse?" I whispered as we stood up. Doug pointed to the kitchen pass-through.

I got my card and walked down the stairs as deliberately as I'd walked up and made sure to step on the two squeaky treads to announce my presence. At the middle landing, I felt two steady streams of cum cascading down my inner thighs. When I turned down the final set to meet Bob, I called out, "Are you decent yet?"

"Yes, and your pie is ready. I do have to get going." I walked up to him and saw a couple of damp spots on his pants and shirt, but the floor was spotless and the towel neatly folded and set on the second step of the stairs.

"Oh, Bob, you of all people should know my pie is always ready. See?" I scrunched my tummy and tilted my pelvis to show off my pussy.

"I watched you walking down. Is that what I think it is?" He pointed to my thighs.

"I should have you smell and taste it to find out. I will only say that I just now fucked my husband right at the top of the stairs, and we both came. I do hope you don't mind. He and I have a close and understanding relationship. It's why you could look but not touch. I did have a wonderful time with you, Bob."

I handed him the card. "Make the total $40."

"The large Chicago Starburst is only $26 including delivery."

I smiled, "We have the menu upstairs, Bob. It's a tip. If your manager questions it, tell her it was for superlative service, with a smile."

He handed me the pizza, grated cheese and peppers, some napkins, my card, a pen, and a receipt to sign. I made a point of turning around, looking all over. "I'll have to set this on the landing for a stable place to sign. Unless you're too late."

"I'm never too late to see your pussy."

I stepped up the stairs again, set the pizza box on the landing, spread my legs, bent over to show the best view of my cunt and asshole, and signed the receipt. I wiggled my butt back and forth while I counted to 30, then picked up the pen and ticket, turned around, and handed them to Bob.

"Thanks, Bob, you know the way out. I'll close the door."

I waited for him to get into the van. I was only going to wave but had a better idea. I walked out to the van and stood next to his door. It took him a few seconds to realize I was waiting for him to lower the window.

"Are you okay, Bob?"

"Yeah, Ruby. You're naked outside on the street."

"You don't know the half of it, Bob. Thanks again."

"This has been the most amazing delivery I've ever made."

"I'm thrilled. Honestly, Bob, I had a great time. Try not to make too much of this, though. Enjoy, learn and move ahead. Next time we order, we'll ask for you specifically. Will you mind?"

He laughed, "I'll keep awake nights looking forward to it. Bye."

I stepped back and waved as he drove forward, "Bye."

Back upstairs, Doug sat at the dining room table, waiting for the pizza. "Thanks for going along, honey. Honestly, it was absolutely accidental. He arrived a minute after you went up to shower. I tried to get you, but you didn't hear, and I went to get the pizza. I just wanted lunch and wrapped the towel around me, breaking my pledge. The towel got knocked off, and you heard most of the rest. Once I'd fallen down nude, I got carried away. He didn't mind."

Doug just smiled. "When I ordered, they told me it was a slow day and would deliver in a half-hour at most. You're usually an hour in the tub, and I wanted to surprise you with the pizza when you finished, but you came down right at the delivery time. You looked so calm and unconcerned I couldn't help myself. I'd turned the shower on but didn't get in and did hear you shout. I was sitting on the step above the middle landing and heard everything from the beginning. When you fell, I peeked around the corner and saw you landed safely. You shouldn't count wrapping yourself in a towel as breaking your pledge, and there's still a day and a half to go. Who knows what will happen?"

"Oh god, Doug, I love you so much. You're always looking out for me."