I can't believe I did this, but it was so hot.
I work with a fun group at a movie theater. It's not uncommon for us to get together after work and have a party. This was one of those nights. There were about 12 of us at Gina's house and we had been having a good time, but the night was wearing on. Debbie, Gina's sister was in the basement on the computer chatting with some of her friends. I had walked in to talk with her and noticed her webcam was on. I was feeling good so I snuck up and started making goofy faces behind her. She didn't even break a smile, she just pointed out that she could see what I was doing on the screen as well as her friends. It was a bit of a buzzkill, so I acted instead like I was going to unzip my pants. This time she smiled.
'I dare you,' she said, looking at the image on the monitor as well as the images from her friends' webcams. There appeared to be three other windows open and three other girls watching and chatting. I decided what the hell, and unzipped my pants. I was getting a little excited and my dick was starting to get hard. Debbie then asked, 'is that all?'
I decided okay, I would strip down to my boxers and see what she said. I undid my belt, unbuttoned my pants and slid then down my legs. On her monitor I could see my image standing their behind her. 'Should I go any further?' I asked her. She swiveled her chair around to face me. She had this odd smile on her face.
'I don't think you'll go any further,' she told me. I looked at the other cams on her screen. I could see the faces of it looked like five other girls between the three windows now.
'Who is watching?' I asked her and slowly hooked my thumbs in the waistband of my boxers.
'Why? Are you afraid?' She swiveled back around. 'We both know you're not going to go any further.'
With that I pushed down on the waistband and stood there behind her with my dick pointing straight out at her. My boxers were now laying around my ankles. I watched the look in her eyes as she saw my naked lower half in the monitor's image. I noticed several of her friends were staring in disbelief as well. She spun her chair back around to face me. 'What were you saying?' I managed to ask. My voice was trying to crack on me and betray my confidence. Plus I wasn't sure what to do now. Absentmindedly my hand started touching my dick.
Debbie's eyes were fixed on my dick, but she managed to look up at my face long enough to ask if I was gonna play with myself for them. I suddenly realized what I was doing. I started to stop, but I decided that this was a once in a lifetime chance and as embarrassing as it might be later, I was really turned on at the moment. I tightened my grip around my cock and began to stroke it in earnest. I knew I wouldn't be able to hold out for long, but I wanted the feeling to last forever. I felt my load rising and managed to ask Debbie if she wanted to watch me cum. She could only manage to shake her head yes. She was completely speechless. I gave one more stroke and a jet of white cum shot out and onto the floor followed closely by two more spurts. I noticed a box of tissues on the computer desk and walked forward to grab a couple. As I got closer, I watched the image of my dick getting larger. As I reached past Debbie for the tissues she reached up and ran one finger through the cum on the head of my cock. She smiled and licked her finger. I thought about asking if she wanted to lick me off, but decided not to push it. I cleaned up and pulled my clothes back on. Debbie turned back to her friends and I can only guess they were all talking about me.
I went back and rejoined the party which was starting to die out. All that was left was Gina, Todd and Angela, his girlfriend. The three of them were out in the back yard. Gina asked me where I had been. They all thought I had left. I told her that I had been down in the basement with her sister. She asked what I had been doing down there. I wasn't sure how to answer, but I figured the best bet was tell her the truth.
'I ended up stripping for her and her friends,' I reported matter of factly.
'How far did you go?' Angela asked.
'Well I kept my shirt on,' I laughed.
'But from the waist down?' Gina asked.
'Bare ass naked?' one of them asked.
'And then some,' I replied.
'And what does that mean?' she said.
'Well, I was a little stiff and needed to take care of that.' I think I might have actually blushed a little bit. Todd kind of laughed, but Angela said,' Damn, I'm sorry I missed that.'
'Me too,' Gina smiled. 'It's my party and I miss the entertainment.'
'I think he needs to strip for us,' Angela added.
Todd didn't say too much. I know he wasn't interested in seeing me strip, but he seemed to be enjoying the position I was in.
Gina looked around and realized the back yard was pretty secluded. 'What do you say, Jon? Care to strip off for the three of us?'
Todd finally threw his hands up. 'Look, I don't really want to see him naked, but if you two do, that's fine.'
I realized it was my chance once more if I felt like taking it. I smiled and said okay. This time I pulled off my shirt first. This time I was going to be completely naked. I took off my pants and then removed my boxers as well. I couldn't get over the fact that I was now completely naked in front of three people outside and in public. I did a sort of street performer 'tah dah' pose and all three of them laughed. I looked at Gina and said, 'Okay, go on and ask. You now you want to.'
Gina smiled and sort of snickered. 'Well you did do it for my sister.'
'You've got to ask or I'm getting dressed,' I teased her.
'Fine, will you jack off for Angela and me as well?'
I looked at Todd and shrugged. 'You can go back inside or just not watch if it's gonna bother you.' With that I started stroking once again. I was able to watch Gina and Angela's expressions as I stroked. They really were enjoying it. It wasn't just a prank to them. Todd just sat there smoking and shaking his head. I don't think he was too wild about Angela watching either, but he figured it would earn him some points to just let her watch. I felt my second load building. 'Where do you want me to cum?' I asked her.
'Just cum on the ground,' she answered. I looked around me at the other neighboring houses. They'd have a hard time seeing what I was doing, and it was nearly 3am so hardly anyone would still be up any way. I wanted to fix the image of Gina and Angela watching me in my mind. I concentrated and then I came. I actually shot a lot further than normal and nearly hit Gina's shoes. She laughed and backed up out of the way.
Once more I got dressed, but this time I called it a night. The story spread around at work, but so far nothing else has come of it.