What A Deal - S01 E25

1 week ago

What A Deal - S01 E25

Read Story: SEASON 1 EPISODE 25

All the women immediately stripped. They giggled while they watched each other fold their clothes and put them on the chairs. I was a little amazed that Cindy could find 4 other women comfortable with stripping and having sex in front of each other. My dick was not responding right away, thankfully.

Cindy came over and whispered her instructions to me. "You are going to be pushed now, so please be patient." She went over to her bag and brought out some toys. I couldn't see what they were. "Okay, slave, on your hands and knees, facing the head of the bed. Let us see that cute little ass and those balls from behind." I got into position, a little more relaxed since I knew all the ladies, but still a little embarrassed by how she described they were going to look at me. Cindy came over and showed me a blindfold. She put it on me and I felt very vulnerable with my entire crotch on display and not being able to see. I felt movement and then I felt a slick finger start rubbing my asshole. Whoa! My wife had not done much anal play with me. It was very stimulating in my position, however, and my dick was instantly hard. I heard Cindy discussing this with the other ladies. It was a little disconcerting listening to them talking about my body like I couldn't hear them. "See, his dick got hard immediately."

Second disembodied voice. "Yeah, and his balls look like they are ready to deliver some cream!"

Third lady. "I just love this. I have never had a man get in this position so I could take the time to study the anatomy of his asshole and balls.

Then I moaned. I could feel something pushing against my anus. It didn't feel like a finger, either. Cindy leaned over to me and said loud enough for everyone to hear. "Now be a good slave slut and let me get this butt plug in your ass. She giggled and the other ladies tittered. I groaned. I had never had anything in my ass and Cindy was pushing a butt plug into it. It was just getting a little painful and uncomfortable when I felt it suddenly slip into place, having gotten past the largest part. It was now seated in my ass and I had never felt anything like it. I just wished I didn't have four other women staring at it while my wife did this to me. I felt several hands run over my ass and balls, feeling them, and then reach up and twist the butt plug. I groaned again. My dick was so hard now that I knew I could come with just a few strokes.

Then I felt the hands stop roaming and suddenly a loud slap was rendered against my ass. I jerked at the contact, but it wasn't too hard. Then Cindy gave them the go ahead. "Okay, ladies, I've always wanted to see a man get spanked, so everyone line up and give him 5 of your best."

I could hear movement and then 'Smack' went the first bare hand on my ass. It was pretty hard, but it didn't hurt too bad. Then whoever it was levied the last four in quick succession, alternating cheeks. It was more humiliating than painful at this point. I had never been spanked in my life and here I was naked on all fours in a hotel room, with a butt plug up my ass, my dick leaking precum, and blindfolded, while 5 women took advantage of the situation.

The second woman took advantage of my kneeling situation and when she smacked my ass, she made sure to make some contact with my balls. Now that hurt and I flinched with each contact. I could hear some comments and giggling. They were definitely enjoying this. I decided to try to concentrate on what I was going to do to get even with Cindy.

I was working on some possible scenarios when the next woman hit me with something that really hurt. I jumped and the pain spread over the cheek where she hit me. I had no idea what it was from that first hit. I was completely surprised. I waited for the next one, tensing for the pain. Then it came on the other cheek and I think I knew what it was. It was a hair brush... and it hurt! I groaned and the ladies laughed. Fuck! thought Cindy said no pain! Shit! suddenly remembered that we never discussed a safe word, so I would have to actually make them quit by getting up if I wanted out of it. I couldn't communicate that we had gone too far to Cindy. I was thinking about that when the third smack struck. Damn! It was hurting. I felt more movement and then could tell that someone was right next to me. Then I heard Cindy whisper in my ear. 'I know we said no pain, but this will only hurt for a second, so please bear with us and honor the bet.' I gritted my teeth and went back to planning what I was going to do to Cindy when she lost the next bet. Fuck It! was going to make her pay... and she had to know that. Why was she pushing me so hard? Is that what she really wanted? Smack! The next one hurt more than the previous one as my ass seemed to be getting more sensitive. Smack! The fifth one came much sooner than expected as they were in quick succession. I yelped a little at the surprise and there was complete silence. It was like they were all staring at my reddened ass. I also could tell that my dick was no longer hard. They noticed, too.

"Well, I guess he's not into pain, his dick has wilted." The voice was unknown, but at least they noticed.

The last two ladies just used bare hands and when they were all done it was quiet for a moment. Then I heard whispering. I felt more movement on the bed and my blindfold was removed. I blinked until I could see again in all the light. Cindy grabbed my arm. "Stand over her, my nice little slave. We have a contest for you." I rose and stood where she directed me, between the bed and the dresser. I looked around and several of the ladies immediately lay on the end of the bed and started playing with their pussies. Damn! As if I didn't have enough trouble keeping my dick under control. It was starting to get hard again and wanted some release. "Honey, none of these ladies has ever had a man jack off in front of them. I told them that you love to do it in front of an audience. But there is a rule." She pointed to the floor. "You have to stand behind that line of tape and when you cum you have to spurt past that line out there or you get spanked again."

I stared at the floor and noticed that it was probably four feet to the other line. Shit, I could probably hit that just from not having sex for a few days from my height, so after being denied for so long, it was going to be easy. Maybe Cindy was taking pity on me. I looked over at her.

"Well, we're waiting. Oh, and you have 3 minutes, starting...." She looked down at her watch. "Now!"

I reacted quickly, but knew that I could get off easy at this point. I went to work on my dick while I stared at the smorgasbord of pussy in front of me. I ran my hand back and forth over my dick and knew it was going to come in a minute.

I got there very quickly and started groaning. When I felt it starting to come, I arched my hips up and made that last stroke. I held my dick up and pointed it toward the finish line. My first spurt went well beyond the four foot mark and I jacked it again... and again.... and again. I finished shooting about six or seven good spurts and at least three of then went past the line. I was just relaxing when I felt Cindy come up and wrap herself around me. Whew! It was over for a while. Cindy led me to the bed and asked me to bend over. I did so and she reached up and slowly eased the butt plug out of my ass. Wow! Did it ever feel good to have that out of there.

She then pushed me back into a chair and I sat. I could hear her talking to the other ladies and they all got up, got dressed, and left.

I couldn't focus on anything. I actually just wanted to go to sleep.

I felt exhausted. After they were all gone, Cindy came over to me and knelt in front of me.

"You did real good honey. Thank you."

I stared at her for a second. "I don't know where that came from, Cindy, but I think maybe you have some explaining to do. Like where you got these toys and these ideas. We don't ever keep anything from each other and I was surprised that these were things you wanted to do. You never mentioned this stuff before. Also, we need to have a safe word if there is going to be pain."

She looked up and gave me a sad and penitent look. She put her head in my lap. "I'm sorry, honey. I didn't mean to do it. I know we said no pain, but once we were in the middle of it, I couldn't say no to my friends. I've known these women thru work for over 10 years and I just got caught up in it. They are the ones that got the toys and came up with the idea for the spanking. Are you terribly angry?"

I thought it over as caressed her. I guess it wasn't that bad. It was just that it was something I never wanted to do or thought about before. My ass was sore, but other than that I guess it was just my macho pride. I had never even desired or thought about having to be a slave. It was also the loss of control. I couldn't imagine doing that often. It just wasn't my style.

I looked down and Cindy and lifted her face up. I guess I could put up with this episode after her bringing me some other women to fuck and have sex with. It wasn't so terrible that I could stay angry at her for long. "Honey." She looked up at me with a pleading look. "Cindy, I love you. will always love you. I was just a little shocked. Why haven't you ever discussed this kind of stuff with me? I mean... I'll get over it, but how come I've never heard about this?"

She crawled up on my lap. "I didn't really think about it until had the control and some of the other women mentioned what they wanted to do. I was just going to enjoy having control and making you wait all day to cum while you waited on us. It was never going to be about spanking or butt plugs or anything until they brought it up after lunch. I just couldn't say no to them. Are we okay?" I just nodded and hugged her. We cuddled like that for a while, but my mind was still racing about all this. I really wasn't my cup of tea, but maybe that's what she wanted. Anyway, it was dinner time now and we finally got dressed and went to dinner, just the two of us. After dinner we were both exhausted and fell asleep early. The next morning we got up and headed home. I was still hoping for some revenge with the next bet. I told her that on the way home.

"Cindy, I do have to say something, however." She looked at me expectantly. "We are going to bet again sometime soon and if I win, you have to know that I will push your limits just like you did mine.