[HHHobo]

Back at Brianna’s I breathed a little easier. Karen had taken the car and gone home. I only had to make it until morning to win my bet with Brianna. “Off with the clothes, Willy!” Brianna ordered.

“Time to do it again, Willy!” Libby announced. I started to grimace, but caught myself just in time.

I asked for some more Vaseline and greased myself up. “Where do you want me?” I asked of no one in particular. The girls glanced at each other and then huddled up. After a few minutes Molly emerged from the group and said, “Do it standing on the bar.”

I climbed up and started in. Masturbating while standing is more difficult than other positions. This was going to take some effort. I worked hard, but I was only growing slightly longer.

“He needs some music,” Rachel suggested. Brianna went to the stereo and put on a CD with an extremely strong beat. “Dance while you jerk the monkey,” she ordered.

I did the best I could. The girls were laughing their asses off. Brian just stood off to one side, grateful that he wasn’t the one yanking his dick in front of six girls. It did begin to get hard. I had trouble deciding what to focus on. If I concentrated on dancing, my cock would start to soften. If I focused on my dick, my dancing would fade, and the girls would yell at me. This was not the most fun I had ever had.

The girls’ jeering continued.

“Out of spunk?”

“Is that all you’ve got, Willy?”

“I guess you’ll disappoint your wife.”

“Don’t double dribble.”

Brianna whispered to all the girls. On her signal they turned their backs to me, bent over, lowered their pants and panties, giving me a group moon. As they did so, they all emitted a Bronx cheer, sounding like a farting contest. That actually took me to a new level. Now I felt that I just might be able to cum again. I quickened my pace. Now they cheered for me, as they could sense that I was going to make it. Soon I could feel that familiar sensation as fluids began to move within me. It wasn’t much in the way of volume, but the orgasm was really quite intense. I sagged when it was over and collapsed on top of the bar.

Everyone at this point was really quite tired. The girls and Brian changed into their night clothes. I got the baby doll back again. We all moved to the entertainment center to see a video that Brianna had specially prepared. I was horrified to find that it was a compilation of all the embarrassing actions I had endured all year. It ran for over an hour. The girls laughed uproariously. Even Brian couldn’t help but laugh. I blushed furiously, managing only a nervous giggle every now and then.

Finally it was over. I waited to see what torture remained. Out came another two-liter bottle of soda. I was given a half hour to drink the entire bottle. Then they put me in another adult diaper and lead me back into Brianna’s Dad’s workshop. There was my sleeping bag, pillow, and pad.

“We’re locking you in, Willy,” Brianna announced. “Make good use of your Depends. Oh! Here’s a couple of spares in case you need them. See you in the morning. Sleep tight. Don’t let the bedbugs bite.”

This was not going to be pleasant. I could already feel my bladder swelling. If only there was someplace else to go. But the workshop offered no options. I lay down and waited about twenty minutes. Then I stood up and let nature take its course. When I was finished I changed out of the old diaper and put a fresh one on. I was tired and figured I could fall asleep right away. I was right on that account.

Several hours later I awakened to the need to urinate. Without a watch I had no idea how long I had slept. I sensed no light anywhere. I knew I couldn’t go back to sleep without relieving myself. So I just went ahead and let fly in my diaper in my sleeping bag. The warm moist liquid gathered round my groin. I rolled over and tried to go back to sleep. To my surprise I was successful.

Some time later I woke again. I was feeling decidedly uncomfortable. The urine was definitely annoying and my bladder was full again. I figured if I peed again in this diaper, I could change to the one dry one I had left. That would get me a few more hours’ sleep, which would probably be sufficient. That turned out to be the case. I did awake with an urge to go some time later, but I sensed it was getting on to morning. There was a sensation of a small amount of light. I tried to hold my bladder, but finally had to empty it into the last diaper. I sat around quite uncomfortably, waiting to be freed from my prison.

Finally I heard the key in the lock and the door flew open. I scrambled to my feet as Brianna ran in. She rushed up to me and gave me a very careful hug, making sure our upper bodies were in contact, but our lower bodies were quite separated. “Congratulations, Willy, I didn’t think you could do it. I’m going to get you the most fabulous dinner at the Lombardie.”


The next Friday evening Brianna and her mother picked me up at seven o’clock. I wore the only suit I owned. It was navy blue with just a very faint pin stripe. I complemented it with a light blue shirt and a hot pink tie. I knew Brianna would love the tie.

I started to get in the front seat, but Brianna motioned for me to join her in the back. “Mom’s our chauffeur tonight.” She grinned. Her mother laughed. I climbed in the back seat and gasped. Brianna was drop dead gorgeous. She had on a black dress that came to mid thigh. It was scoop necked and showed just a tiny bit of cleavage. I can’t begin to describe all the rest of her clothes and jewelry and make-up, but it was stunning.

“You look great!” I stammered out.

“Thanks,” she replied.

We carried on small talk for the fifteen minutes or so that it took her mother to drive us to the restaurant. When she dropped us off, I thanked her for the ride and she drove off.

We walked into The Lombardie and Brianna gave her name to the host. I expected us to be escorted to a table in the main dining room, but instead we were taken to a small room upstairs.

“Don’t worry, Willie,” Brianna said. “Everything is prearranged. You’re going to have the meal of your lifetime.”

We entered the room and sat down on either side of a table that could have sat six. Immediately a waiter entered and poured us each a glass of Champagne. I looked at Brianna strangely.

“I told you not to worry. We’re not going to get into trouble. Just sit back and enjoy yourself.”

Soon a waitress showed up with a huge tray of seafood appetizers and placed it on a buffet table along one side of the room. She invited us to take a small plate and help ourselves. Everything was delicious. I could identify shrimp, clams, crab, and lobster, but there were a lot of others that I didn’t know. I’m not sure that I really want to know what I ate. But it was surely good.

A small salad followed and then a crab casserole, accompanied by a glass of delicious white wine. I think they said it was a Sauvignon Blanc. The main course was lamb chops, my favorite meat. It was accompanied by garlic mashed potatoes and the best green beans I have ever eaten. With this course we had a glass of Pinot Noir. Dessert was a chocolate mousse.

The most surprising thing about the evening was how well Brianna and I got along. We talked warmly about all kinds of topics. She repeatedly congratulated me about what a good sport I was and how well I had held up last weekend. I admitted I found some of it fun, especially in retrospect. We even plotted a bit about how we might trap some of the others into delicious dilemmas.

“You’ve really suffered enough, Willy,” Brianna allowed. “It is fun picking on you, so I may get tempted again. But I’ll try to go after someone else for at least a little while.”

“Thanks, I think,” I replied.

Brianna giggled. “You know,” she went on. “Maybe opposites do attract. You and I don’t really do things the same way, but there is something that draws us together. I really am very fond of you. You can really trust me not to do anything really dangerous to you.”

“I know,” I answered. “You always seem to have a twinkle in your eye when we are playing our silly games. It’s not that you’re a true sadist. By the way,” I changed the subject. “This dinner must have cost a fortune. I really thank you, but there’s no way I can ever repay you.”

“Not to worry. My parents can afford it and you deserve it. Besides, I got to enjoy it, too. I had no trouble talking them into it. They really like you. I know you really like Veronica, and I am hoping that Jamie Knowles will give me more attention, but somehow I feel that you and I are going to hook up someday.”

I sort of shuddered at the thought, but I knew she had a point. There was certainly a sort of chemistry between us. And for all of the stunts that Brianna had pulled, she never really let the nonsense get to the point that I was truly publicly embarrassed. All those pictures could easily have ended up on the Internet, but they hadn’t.

As I was musing over the situation, the dessert dishes were being cleared away. Brianna caught me completely by surprise. He walked around the table, took me by the hand, and had me stand up. She wrapped her arms around me and gave me a huge kiss. No tongues were involved, but the warmth of her gesture astounded me even further. There was no doubt that my image of Brianna was changing.