[Fiction] The Sleepover Club

[HHHobo]

Stay Tuned. It may not be at the end of 5 weeks, but Willy comes out OK in the end.

[HHHobo]

The next morning Karen supervised my preparations. I did wake with a boner, so now I had two points. After I hurried through an ice cold shower, my sister handed me a pink paisley thong. I dressed in the baggiest pants I could find. Even those wouldn’t fully conceal a full fledged woody.

The rest of the week was much like Monday, but I wasn’t embarrassed as badly as I had been in geometry. That Tuesday Brianna made me take a Viagara before school. But I didn’t get called to the board at all. I think only the girls from the club knew I was sporting a long, hard one. I ate a lot of salad and fruit for lunch under the direction of the girls. The evening dares stopped. I think they were having trouble coming up with ideas. Two of the three days I woke up with a hard-on, but the other day I was soft. I had a narrow four to three lead.

Friday night I had a basketball game. The freshmen played at 5:30. I was a starting guard. The entire club came to the game. They all really cheered hard for me. After all the grief I had been getting from them, the cheers felt good. I responded with my best game of the year – 18 points, 10 assists, 5 rebounds, and only 2 turnovers. We won easily. In the locker room, the coach looked at me and said, “Martin, you had the worst practice week of the year. I have no idea where that performance came from. But I’m grateful and I congratulate you. But don’t do it too often, or they’ll take you from me and put you on JV.”

[stacyz69]

great story... making me nostalgiac of all those sleepovers i had this summer

[HHHobo]

Saturday morning I got my homework done for the weekend. In the early afternoon I helped my dad clean out the basement. At 3:00 I got Mom to drive me to the mall, where I was meeting the club. Karen spent the night before with Cicely Warner, her best friend. She met us at the mall. They were all there before me as I walked into the food court. Immediately we were all up and moving directly to Victoria’s Secret. There Karen picked out eight very skimpy pink thongs. I had to go up to the counter and pay for them. I tried very hard not to look in the clerk’s eyes. I could tell she was a very good looking woman in her 20’s. She asked me a couple of questions. “Are these a present for your girlfriend? Are you doing this on a dare?” I wanted to answer, but I was too embarrassed to open my mouth.”

We left the store, but I was carrying a bag that said very clearly, “Victoria’s Secret”. Brian left us to go to a book store and a music store. Karen had to go home to do her chores and homework.. The girls dragged me around from female clothing store to jewelry store to a make-up counter to an earring kiosk. I had never been to any of these places before. They kept asking me questions about how things looked, what I thought about this, and did this look good. A few purchases were made, but mostly the girls were just looking. I couldn’t wait for it to be over. We stopped at a costume shop, but they didn’t let me go in. This had me a little worried. I was even more worried when they came out with a package. My worries deepened further when they wouldn’t let me see what they had bought.

Libby grabbed me by the hand and pulled me over to a bench. She was carrying the bag from the costume shop. “We’ll wait here, while you go get the “you-know-whats”, she said to the rest of the girls. They took off, leaving the two of us to talk.

“How are you handling all of these forfeits, Willy?”

“It’s all very embarrassing.”

“Isn’t there any fun in it for you at all?”

I paused and thought. It seemed I was always getting myself into these positions. Back in middle school, before the club was founded, I always seemed to lose the games more than others did. I ended up doing things I would never do voluntarily but I never chickened out. I guess maybe there was something about it that I liked. “It’s weird, but there is something of a thrill to at least some of it.”

“Do you have any idea what my ‘date’ with you will entail?”

“I’m beginning to think I’m going to have to dress up as something.”

“Nice deduction, Sherlock! It’s also a hint about something coming up at our next sleepover.”

“Does it involve crossdressing?” I asked Libby.

“Sort of,” she replied. “Believe me, it could be a lot worse.”

Our talk drifted to school and teachers and other students. We talked about whether we should expand the club the next year. There were some kids a year younger who used to come to our sleepovers who would be freshmen next year. We could add them. Both of us seemed to think it was a good idea.

Soon the others returned. Molly spoke for the group. “Have him change first. Then put the finishing touches on. We’ll be down the line ready to take some pictures. Do the food and flick things. We’ll meet you later.” Rachel handed Libby another package. Then all except Libby turned and left.

Libby turned to me and handed me the bag from the costume shop. “Go into the Men’s Room and go into a stall. Take ALL of your clothes off and put on what’s in the bag. Put your clothes in the bag, including shoes and socks. Then meet me back here.”

I followed her orders. Once I was naked, I opened the bag and took out a plastic zipper bag that was labeled “Hippo Ballerina”. I groaned, but continued. I put on this pink garment covered with sequins and other sparkling ornaments that came in two parts. The big part was a jump suit with the zipper in the back. It also had a metal loop at the middle that made the wearer appear to have about a sixty-inch waist. Once I had it on, it was very awkward. I would fit through doors only by compressing the loop. The little part fit over my head. It had ears that stuck off the top, but nothing much more. I had it all on, stuffed my clothes in the bag and went back to Libby. It was all very embarrassing.

Libby had me sit down on the bench. She opened the small package and took out a pair of ballet shoes. These she proceeded to put on my feet and tie around my calves. Then she took out some make-up and went to work on my face. When she held up her mirror to my face, I saw the face of a female animal looking back at me.

Off we went from one end of the mall to the other. Our destination was the food court, just about as far from us as could be. I felt so self-conscious walking along in this outrageous outfit. Intellectually I knew that no one could recognize me, but that was cold comfort. I could feel the blood vessels in my cheeks dilating. I reached a hand up to one cheek and felt the warmth.

After we had gone about a hundred yards, Molly stepped out and shot a bunch of pictures. We walked a little farther and Rachel stepped out of the shadows. Libby told me to spin around. I did so and felt markedly silly doing so. Our next hurdle was Colleen. As we saw her, Libby ordered me to pretend to dance. I pirouetted and leapt, spreading my arms, and acting like a total ass. Colleen snapped away with her camera. Only Bridget and Brianna to go. I spotted Bridget up ahead. Libby gave me no directions, so we continued to walk toward Bridget. When we were about ten feet away, Libby told me to turn to the right and stand still. As I did so, I gasped. Here came Brianna straight toward me with a huge cream pie. With a twinkle in her eye and a satanic grin on her face, she smashed right in my face, giving it a twist to effect total coverage.

I staggered back. Bridget was snapping away with the camera. The other girls had followed us. Colleen quickly gave me some paper towels, while Rachel and Molly wiped up the floor. We didn’t want to get in trouble with mall security. Once I was clean Libby led me off to the food court. The others went in another direction, waving goodbye to us. Once in the court, Libby chose a table far from the fast food restaurants. She gave me some money and told me to go to McDonald’s and get a Big Mac and a strawberry shake for myself. She knew I didn’t like all the extra stuff on the Big Mac and I detested strawberry shakes. After McDonald’s, I was to go to Taco Bell and get Libby a chicken taco and a diet coke.

The jump suit had no pockets, so it was hard to juggle the money and the food. As I walked to the counter, I got plenty of funny looks and a few rude comments. At McDonald’s counter, the girl burst out laughing. Over at Taco Bell the girl behind the counter asked why I was dressed like that. I mumbled something. I was so embarrassed. It was a good thing the jump suit was so wide. I was sporting a massive boner.

I finally got the food back to the table. We ate in silence, as I tried mightily not to gag. I managed to get and keep it all down. Then Libby sent me back up to get two sundaes. Once more I had to contend with questions and comments. I was afraid that Libby would make me eat the sundae in some weird way, but that didn’t come to pass.

Fortunately the multiplex wasn’t far away. Libby picked a chick flick, “My Handsome Prince”, and sent me to the counter to get tickets. I kept getting funny looks. It would be good to get inside in the dark. When we did get in, Libby directed me to the next to top row in the stadium style theatre. She selected two seats in the middle of the row. Once we were seated, she reached up and tied a blindfold around my head. “If you’re good, I’ll take it off when the feature starts.”

There wasn’t much I could do except sit there. I sure didn’t want to wander around and be noticed. I wasn’t about to try some silliness that would make my forfeits even worse. I heard the umpteen trailers. Finally I heard the music for the feature and Libby took the blindfold off. I thought someone was sitting behind us, but I didn’t want to draw any more attention, so I just kept my eyes on the screen.

About twenty minutes into the movie, Libby sent me to the refreshment stand to get popcorn and soda. Oh! Good! More embarrassment! When I returned, I didn’t see anyone in the last row behind us. I assumed my earlier impression was mistaken. I sat down and gave Libby her soda and placed the big bucket of popcorn on my lap. It was a little difficult, since I still had a rock-hard wiener.

We ate about half the pop corn, before slowing down. I sat the bucket on the floor. We both kept sipping our sodas and watching the heroine trying to find a way to get the hero to notice her. All of a sudden I felt an icy cold hand grabbing the back of my neck. I leaped up and almost screamed. Of course it was Brianna. She and her cohorts had been on the floor behind us. They laughed at my discomfiture. “I have a test for you, Willie,” Brianna chortled. “If your dick is soft, we won’t bother you again tonight. But if it is hard, you have to pay a penalty.”

She told me to sit back down. The back of the jump suit was unzipped down to my waist. An arm reached in and encircled my body. A hand grabbed at my manhood, still rigid as a flagpole. “Gotcha!” called Brianna, and everyone I laughed. Bridget asked Libby for the pop corn and she handed it to her. Brianna held the back of my jump suit open and Bridget poured the pop corn into the suit.

“Now finish your drink, Willie,” ordered Brianna. There was still at least twelve ounces of soda in the cup. I sucked on the straw until it was all gone. “Now you cannot go to a bathroom until you get home. Libby may, but you may not. If you pee your pants, you have to be naked the rest of the night.”

We sat there watching the rest of the movie. The girls in the back row kept making water sounds. I squirmed more and more as my bladder swelled bigger and bigger. When it was over, we left and headed for the farthest part of the parking lot. I saw Karen’s car parked there. So that was our ride home. But it wasn’t as simple as that. The girls made me strip naked and sit in the middle seat in the back seat. Then they took turns playing with me. It was the old frustration game. I came close to cumming, but they always broke off just before release.

Karen took the girls home first, taking a route that was as long as she could possibly make it. I was really getting in trouble now. The only thing preventing me from erupting in piss was my boner. It didn’t help that Karen went out of her way to hit every bump she could. Once all the girls were dropped off, I was given back my real clothes. I gratefully put them on as Karen drove slowly home. When she pulled in the driveway, I leaped out and ran for the bathroom. Thankfully I made it just in time.

[Memories for Life]

Yes, that's the chapter that I'm always glad to read. Well done and I'm looking forward to the next "activity"!

[HHHobo]

Sunday was a quiet day. Unfortunately I woke up without a boner. Now I was down six to four. The parents went to the country club late in the morning to play golf. They would be gone until dinner. I had been told I had to let the winners know any time that the old folks would be gone. When they told us at breakfast, I waited until the meal was over. I went upstairs and called Libby on my cell phone. She told me to get naked when my parents left and wait for further instructions.

I went to work on my homework. I’m really a very good student and I like most of my subjects. My English teacher sucks, but the rest of them are OK. My history teacher is really great. I always liked reading about history, but I never liked it in school until I got Mr. Kilgore. He was very popular with the better students. He made the subject come alive. Other history teachers just made us memorize a lot of names and dates.

In any case I put about three hours in on my homework when the phone rang. It was Colleen. “Bridget and I are coming over to see you in about half an hour. We’re riding our bikes, or we’d be there sooner. Don’t change your state of dress.” Then she rang off.

I worried about what they had up their sleeves. I still had a bit of work to do on a PowerPoint that I was doing for physics on the life of Isaac Newton. I had just about finished, when the doorbell rang. “You have to get it. I’m too busy,” laughed Karen. I looked out the window to see who it was. If it was other than Colleen and Bridget, I was cooked. Fortunately it was my two friends. Still it was embarrassing to answer the door naked and my willie sprang to life.

I walked downstairs to the front door. I hesitated slightly and the bell rang again. If it had been Brianna, she would have been pounding on the door and screaming. I opened the door and both of the girls smiled. “I see you’re glad to see us,” quipped Bridget. I don’t think she knew she was quoting Mae West.

The girls came in and we went downstairs to the family room. “We need to talk to you, Willie.” Colleen said. “We all talked on the phone last night after we went home from the mall. We have decided that we are being far too harsh on you. We don’t want to let you off the hook completely, but we do want to ease up a bit.”

“Thanks,” I answered. “It has been annoying. I usually get excited when I have to do embarrassing things. At least some of what has happened has been just aggravating.”

“Most of us have felt bad for you in the last couple of days,” Bridget added. “That’s one of the reasons we went to the game and cheered so hard for you on Friday. Even Brianna thinks we have gone too far.”

“Thanks, again. That really did help my play. Coach gave me great compliments after the game.”

“Here’s the deal,” explained Colleen. “The panties, boner, and masturbation rules are still on. You have to be hairless below the neck for the sleepover, but not until then. But all else is off, except for the forfeits at the sleepover. You, Molly and Rachel will have to streak, and you will be doing a lot of crossdressing.”

I blew a sigh of relief. “Thanks,” I muttered. “I think I can actually have some fun with the ones that are left.”

“By the way,” Bridget asked. “How are you doing in the boner contest?”

“I’m behind six to four.”

“I’ll bet you’d love to whack off,” Colleen offered.

“You better believe it.”

“Wait here,” Bridget said. She grabbed Colleen and they ran back to Dad’s workshop. In a few minutes they returned.

“How about a side bet that costs you nothing?” queried Bridget.

“What is it?” I replied.

“If you can win the masturbation forfeit, Colleen and I will be your slaves for a weekend.” Colleen nodded to show her agreement.

“Sure, why not?”

Shortly they left and the rest of the day was actually boring. I hadn’t had that feeling for a while.



The next four weeks went by quickly. Basketball season was winding down. I continued to play well. Brian and the girls came to all of the home games and cheered for me. I know it helped. The last home game was the Saturday before Presidents’ Weekend. Here I was to exact a little bit of revenge. The team we were playing was the weakest in the league, but the girls didn’t know that. I bet them that I would score more than twenty points. My highest so far that year was eighteen. If I succeeded, I could do one of two things. I could reduce the hours of crossdressing in my forfeit by the number of points I scored over twenty. The other option was that I could claim a forfeit from any individual girl for each point I scored over twenty. On the other hand, if I failed, the crossdressing was to be extended in hours by the number of points that I was short of twenty.

Not only did I know we were playing a weak team, but I got my teammates to help. I told them I had a bet with the girls who were cheering for me. I didn’t tell them the stakes, but they agreed to feed me the ball, as long as we had a safe lead. The safe lead happened almost immediately as we got off to a 12-4 advantage. It only got easier after that. We won 76-20. I scored thirty points. I would have scored more, but the coach took me out two minutes into the fourth quarter. I pleaded to go back in, even telling him about the bet, but not the stakes. He refused. He didn’t want to run the score up any more and he wanted other guys to have playing time. I accepted that. I had already won the bet, so I was satisfied.

I met up with others after the game and we went to McDonald’s for dinner. I told them I would take the forfeits, but wouldn’t collect on them until much later in the spring. In truth, I didn’t know what I wanted to do. I had to think about it.

I actually got the nerve up to ask Veronica out to a movie. I was elated. It was the first time I had actually asked anyone out. We have a tandem bicycle. I asked Veronica if she would like to ride it to the Cineplex. She thought that would be fun. The next Saturday I rode the tandem over to her house. It felt funny riding the tandem alone. Once I got there and she hopped on, we had a wonderful time. It was cold, but we were all bundled up.

At the theatre I let Veronica choose the film. To my surprise she chose the current James Bond. “I’m really a big fan. I have all of them on DVD. My favorites are the early Sean Connery versions. Roger Moore really sucked,” she explained.

We had about a half hour before even the trailers started, so we just sat and talked. I was surprised that we shared many of the same interests. This was exciting. I might be getting my first real girlfriend.

When the movie was over, I asked Veronica if she wanted something to eat. She said she did, so we pedaled to the nearest fast food place, a Wendy’s. Afterward we rode the tandem back to her house. When we arrived, she jumped off and gave me a big hug, and said how much fun it had been. I was delighted and rode home on a cloud. In the coming days we began to talk on the phone, text message, and IM each other.

Going into the last week, I still hadn’t yanked my doodle. It was actually becoming the normal state. I did have the problem of wet dreams. I suppose it helped relieve the pressure. It also helped stimulate “Boner City” in the mornings. Karen got tired of checking up on me, and took my word for it. I could have cheated, but I didn’t. Since the girls had let up on me, I figure I owed it to them. The bad part of the wet dreams was that I always ended up soft after they were over. Consequently it was a dead heat at the beginning of that last week.

The sleepover was starting Friday night. I had five mornings to go. If I were hard for four of them, I would win the bet and avoid slavery to Karen over Spring Break. She can be every bit as creative and sadistic as Brianna, if you give her the chance. Monday morning I woke up hard and called to her through the bathroom door. “Just a minute, “she replied. “Now I want to see for myself. The score is too close. I’m not going to let you cheat.”

“I’m not lying,” I protested.

“I’m just making sure.”

The door of the bathroom opened and Karen came out just wearing a towel. I just stood there smiling and naked. Karen reached down and grabbed my woody to make sure it was hard. It was. The move caused the fold in the towel to come loose and slide off her body. Karen shrieked, try to cover herself, and run back into the bathroom. The door slammed loudly, and I laughed my ass off.

Unfortunately for Karen, that was the only towel she had. We both take towels from our bedrooms when we shower and put them in the hamper when we are done. Karen was now safe in the bathroom, but she had neither towel nor clothes. She pleaded with me for help, but I had her this time.

“I’m sitting right here in the hall,” I stated. “If you WALK out of the bathroom and ask me politely, I will return your towel. Your other option is to run for your room. I have my camera out. If you choose the second option, I use the camera.”

She swore at me, but I paid her no mind. Time was on my side. I had so much less to do to get ready than she did. Finally she agreed. The door opened. She casually strolled over to me and asked, “May I please have my towel back?”

“Yes, you may,” I answered her, handing the towel over. She turned on her heels and returned to the bathroom. She had appeared calm, but her face was very red. My sister has a great body, but I was more interested in seeing how much I could embarrass her.

Tuesday I awoke about an hour and a half before the alarm was to go off. The stimulus that broke my sleep was a large deposit of semen in my tightie-whities. I cleaned myself up and put on a clean pair. I got back into bed and tried to think of the most erotic things I could. But it was no use. My dick stayed soft. I went back to sleep. When the alarm went off, I was still flaccid. I admitted as much to my sister. Now I was two points behind.

I had better luck on Wednesday and Thursday. Karen checked me out both days. I was rock hard for her each time. I just needed to wake up hard on Friday to avoid humiliation at the hands of my sister.

Thursday night I finished my homework by about nine and I booted up my computer. I started searching for anything that would turn me on. I found some great pictures of naked women, read some erotic stories, even visited some fetish sights. When I crawled into bed an hour later, I had a raging hard-on. I could only hope it would last until morning. My great fear was another wet dream. I prayed that I hadn’t overdone the stimulation.

Morning came. The alarm awoke me from a sound sleep. I reached down and found a throbbing penis in my briefs. I didn’t care about Karen’s reaction. I raced into her room flaunting my pulsing pud. She yelled at me, but I still didn’t care. She conceded defeat. I was off the hook for Spring Break.

[Memories for Life]

I would of thought that Willie only had to think of his sister nude without her towel would be enough for him to have a boner! Another great chapter! Even with the girls easing up, I'm wondering if the next sleepover will be another "Willie gangbang"!

[Trav90]

Originally Posted by Memories for Life

I would of thought that Willie only had to think of his sister nude without her towel would be enough for him to have a boner! Another great chapter! Even with the girls easing up, I'm wondering if the next sleepover will be another "Willie gangbang"!

I hope the next sleepover is!

[emmah100]

Did anyone catch if willy is still a virgin? lol I'm kinda pulling for him to get get some sort of symphony sex...

[HHHobo]

Presidents’ Weekend


The sleepover was back at Brianna’s. Her parents were going to be out most of Friday night. Chances were that they wouldn’t even look in on us when they returned. They would just call down to the family room to say “Good Night”. They were also going to be out and about most of Saturday. Karen had agreed to provide us with transportation on Saturday afternoon. I think she just wanted to see me cross dressed. It’s easy to see why we planned the sleepover for Friday night to Sunday morning. There would be plenty of time for homework on Sunday and Monday.

That day at lunch the winning girls had confronted me. “OK, Willie, what is it going to be?” Bridget challenged.

“Come on, Willie, be daring,” added Libby.

“You know you want to do it,” teased Colleen.

Brianna just sat there and grinned. I already knew my decision, but I wanted to string it out a bit. I pretended to ponder. I looked around at the four of them. Molly, Brian, and Rachel sat off to the side, watching the confrontation.

“You really want me to take the big challenge, don’t you?” I countered.

“It will be a lot of fun,” Bridget replied.

“For you maybe,” I said right back.

We sat and stared at each other for a few more moments.

“All right, I’ll take the challenge. You may do your worst.”

They all cheered. Brianna finally spoke up. “Willie, if you make it all the way through the weekend without even one complaint, I’ll take you out for dinner at The Lombardie.”

(Wow! That’s the best restaurant in the city. I’m going to do everything I can to win this one.)

Eight o’clock that night found all of us in Brianna’s family room. They made Rachel, Molly, and me strip immediately. Brianna and Bridget took charge of me. Now I was naked, and I assumed that the streak was coming up soon. But they were going to apply the feminine touches. They had requested that I not shave. They wanted to do it themselves.

I was ushered into the shower stall. This time I got lucky and it was warm. Upon emerging I was coated in shaving cream. All four of them went to work on what little hair I had. Soon I was smooth all over. Then the nail polish came out and all my fingernails and toenails were soon hot pink. Make-up came next. The surprising addition was a long purple wig. When they put it on my head, the hair went half way down my back. I hadn’t blushed until that came out, but now I was beet red. Still I made no complaint.

When they brought me back into the family room, I saw that they had done similar jobs on Rachel and Molly. The two of them were made up like a couple of whores. “Now for the finishing touch,” announced Brianna. Colleen walked in with three plastic shoe bags. Each contained a pair of sandals with a two-inch platform and four-inch heels.

I had to have help just getting them on. Molly and Rachel had theirs on before me and stood up. They had trouble walking in them. I didn’t see how I was going to succeed. When I was finally helped to my feet, I couldn’t even take a tiny step without teetering. Twice I had to grab hold of furniture to keep from falling. My calf muscles ached and my feet felt like they were lashed with rope. How do women manage to wear these things?

“Now for a group portrait!” Bridget announced. We stumbled over in front of the fireplace. Rachel and Molly were only a little bit better than I was. They seldom wore heels, and never any as high as these. The two of them stood on either side of me and the cameras clicked away. This was potential blackmail material, but we were very good about keeping things among ourselves. I wasn’t worried.

Brianna now described a problem. “I came up with a truly great idea for a streak, but I forgot about the weather. If we try to do it tonight, you’ll be outside naked for far too long in 35o temperatures. Would you be willing to wait and do my sensational streak in warmer weather?”

The three of us looked at each other. I said to them, “I will, if you will. These streaks are embarrassing, and potentially humiliating, but they are exciting.”

Rachel countered. “I’ll be happy to wait, if we can omit the shoes.” Molly agreed with her.

I turned to Brianna. “How about it?” I asked.

“OK, that’s reasonable, I suppose.” She shrugged her shoulders.

Rachel and Molly were allowed to put some clothes on, as the streak was their only remaining forfeit. I never learned their other forfeits. Brianna and Bridget did insist that they leave the makeup on.

“Now it is time for Willie to relieve some pressure,” Colleen announced with a gleam in her eye. “Come kneel down over here.” She pointed to a spot where a big towel had been laid out on the floor. I had had a major boner ever since I had taken my clothes off. I knew that I would shoot my wad in no time at all.

Libby asked me, “Have you kept your vow not to masturbate since MLK weekend?”

“I have!” I stated firmly.

“Have you cum at all during that period?” Libby went on.

“I had four or five wet dreams,” I admitted.

The girls all giggled and I blushed some more.

“All right, ladies, let’s have a poll,” Brianna pronounced. “How long do you think it will take Willie to come?”

Molly spoke first. “One minute!” (That’s probably a little low, but not by much.)

Bridget guessed four minutes, Colleen two and a half, Rachel said five, and Libby went all the way up to ten minutes. Brianna opted for a minute and a half. Brian declined to guess, but he was grinning at my predicament.

“Closest person gets to direct Willie’s first crossdressing. Farthest has to clean up Willie and the floor any way that the winner decides. (Brianna or Colleen will win; Libby is in big trouble.)

Brianna asked Brian to be the timer. The girls all had their digital cameras out ready to record my orgasm. Brian called “GO!” I started stroking my turgid tool. (This feels so good! I’m not going to last any time at all.) I was breathing heavily almost at once. Precum dripped from the end of my dick. I thrust my hips forward. The girls yelled encouragement. “GO, WILLIE, GO!” It was like they were cheering for me on the basketball court. (Here it comes. What a feeling! Once! Twice! Five shots! ) I sagged back on my calves. The girls applauded wildly. I had left a real mess on the floor. (Poor Libby!)

“Two minutes and twelve seconds,” Brian announced. Colleen had won. Libby blushed. She knew she was in for it now. Colleen turned to her and said, “First clean up Willie,…………………. with your mouth.” Libby gasped, but she proceeded to lick the remains of my cum off my prick and groin area. It helped her that I was shaved smooth. Colleen now eased up and handed Libby some tissues to do the floor. (She’s lucky it wasn’t Brianna. She’d be licking the floor.)

Now Colleen turned to me. “It’s starting to get a little late. Let’s dress him for bed.”

“But he has to keep the heels on until we actually go to bed,” suggested Brianna.

I almost groaned, but caught myself just in time. I knew Brianna would call that a complaint. Bridget went upstairs and came down with a frilly baby doll that I had to wear. Even though it was really girly, it was good to have some clothes on.

We played T-or-D for a while, but it was nothing spectacular. Clothes were lost by people chickening out on dares. Colleen had to call a boy up and tell him he had nice buns. Rachel had to call her crush and ask him to the movies on Sunday. (He accepted.) The condition was that Rachel had to let him do whatever he wanted to in the theatre. I had to run around the back yard for five minutes with the baby doll flying up while the girls tried to paddle me. I took a few hard shots to the tush. More clothes were lost. Now I was seeing some boobs and butts of my torturers. Molly had to do a pole dance. She was really sexy. My rod stiffened again. Brianna had to a strip tease for Brian and me, including flicking her clit. In true Brianna fashion, she took it over the top and went to organism. She squirted all over my face.

Just as I thought it was all winding down, Libby dared me to cum as many times as I could for the entire sleepover. This was really surprising, as Libby was usually one of the most conservative members of the group. It really wasn’t possible for me to strip instead. That sort of defeated the purpose of the crossdressing. I thought I might have some fun if Brianna would cooperate. I turned to her and said, “Let me get revenge?” Brianna was still naked. Her eyes twinkled. She answered, “OK, Willie, do your worst.”

I had her lie down on her back. Then I took off the baby doll and knelt down with one knee on either side of her body. My butt was right over her pussy. I looked down on her cute, round boobs. I took my cock in my left hand and started stroking. Brianna started teasing, “Come on, Willie, can’t you go faster than that?”

Others joined in. “You came a lot faster this afternoon!”

“Your dick was bigger earlier!”

“Don’t rub it raw!”

In fact, my prick was beginning to get a little raw. If I kept doing this I would need some Vaseline. Rachel, Molly, and Brian started in on Brianna. “Catch it in your mouth, Brianna!”

“Having fun yet?”

“Hump for him, Brianna!”

She responded to that and began to bounce up and down, rocking into my ass and making me lean forward. I could tell from the look on her face that she was beginning to get turned on.

As I got hotter and hotter, I arched my back, pulling away from Brianna. She slid her hand past my leg and started playing with herself. I was so focused on my own condition that I paid little attention to her. Once more precum dripped from the end of my cock. It seemed to land right between Brianna’s breasts. I was getting close, and it looked as if Brianna was too. Finally I exploded and launched a stream of jizz right into Brianna’s face. She responded by opening her mouth to try to catch the next load. Dead Center! As I was about to cum for the third and last time, I felt a wet sensation on my butt. Brianna’s pussy juice had nailed me as we both orgasmed.

There was a cheer from the rest of the group. I collapsed on the floor next to Brianna. Bridget got a couple of damp towels so we could clean up. After getting the love juices off my body I slipped the short nightgown back on. We all stood around in a circle, sort of staring at each other. Libby observed, “We can’t top that. Let’s turn in.” Her suggestion received unanimous approval and we headed for our sleeping bags.

[Memories for Life]

Excellent new chapter! Willie is embarrassed slightly but for the most part has gotten the chance to enjoy himself. At least he hasn't been forced into public in his cross-dressed appearance! I wonder if Rachel's crush has a buddy who'd like to double-date with Wilma to the movies on Sunday!

[HHHobo]

By the time I woke up the next morning, Brianna’s folks had already left. The girls were all standing around me. “Time to try again, Willie,” Libby demanded. I almost complained, but caught myself just in time.

“I need some Vaseline,” said I.

Bridget disappeared and returned in a few minutes with the slippery lubricant. Slowly I took the baby doll off and rubbed the Vaseline all over my member. Reluctantly I began pulling on it as I stood in the midst of the girls. This wasn’t really what I wanted to do first thing in the morning. My willie wasn’t really into it either. It was slow to swell and lengthen. Finally it began to harden as the blood vessels dilated and admitted fluid into the spongy tissue. (I learned that in honors biology.)

As I was finally turned on, I dropped to the floor and stroked harder and harder. I just wanted to get it over with. I wasn’t horny. I didn’t need release. I was just doing this to please the girls. The competitive side of me didn’t want to lose to Brianna or anyone else. No precum emerged this time, but I did get two respectable wads of cum out of my dick. After not whacking off for five weeks, I had now done the deed three times in just over twelve hours.

I cleaned up, put the little nightgown back on, and wandered upstairs to find some breakfast. I found some juice and cereal to my liking. I sat down and read the sports page and comics for a while. Just as I was finishing, I heard Rachel calling me to return to the family room.

I knew I couldn’t ignore the summons. I took myself back downstairs to meet my fate. First I got another shower, thankfully warm. Then the feminization continued. My nails were still very pink, but my makeup had to be redone. This time it wasn’t quite so extreme. I got a new pink thong and a bra. Water balloons were inserted inside the cups to provide some substance. Next came a low rise, navy blue miniskirt that looked like nothing but a band of material with one elastic side. A tight-fitting pink top completed the clothing.

Next came a new development I hadn’t anticipated. Brianna brought out a cut potato, a bottle of alcohol, some ice, and a sharp needle. “All the girls have pierced ears, Wilhemina. Now you’ll join them.” They iced my ear lobes for about five minutes until they were good and numb. Brianna slid the potato under one of my lobes, and stuck the alcohol-sterilized needle through it. I only felt a pin prick. Quickly they slid a stud into the new hole. The procedure was repeated for my other ear.

“Don’t worry, Willie,” Colleen assured me. “The hole will close up Sunday.”

The wig returned and the girls brushed and combed it into shape. Then some very girly pink sandals were placed on my feet. Rachel handed me a navy blue purse with pink trim.

“Time to meet the world!” announced Bridget. We all put on coats. Once again mine was pink. We headed out the door and down the street. I kept trying to work myself to the middle of the group. Finally Brianna ordered me to walk in front. Reluctantly I obeyed her wishes. Brian and the girls gave me instructions on where to go. Fortunately there weren’t too many people out in the cold weather. We did walk far enough to get to a strip mall. There we went into a Walgreen’s. They made me buy some nail polish with glitter in it.

That was it for that session. We walked back to the house. So far things hadn’t been too bad. It had to get worse. Brianna didn’t just throw away deals like The Lombardie. I was definitely anxious about what was coming this afternoon and evening.

When we got back to Brianna’s, I was ordered to strip again. Once I was bare and shivering in front of the rest of the group, Libby handed me the Vaseline. I grabbed a seat on a bar stool and greased up my organ. Slowly I started stroking away. There was a certain soreness present. It was not in any hurry to get bigger or hard.

“Come on, Willie, can’t you do it,” jeered Brianna. The others all laughed, except for Brian. I could see that he felt sorry for me. I don’t think he could have gone through the things that I did. Actually I didn’t mind most of it. I was used to being naked in front of these girls. Now I was even tolerant of beating off for them. At this point it was just tiresome trying to cum again so soon.

It was at least five minutes before my dick neared its maximum length. It was a few more minutes before it got hard. I still didn’t feel very turned-on. Some of the girls were getting bored. Rachel and Colleen were having a side conversation. Brianna had picked up a copy of Cosmo. “Let me know when he is about to cum,” she requested. On the other hand, Bridget, Molly, and Libby were trying to tease me with their bodies. Bridget didn’t have much in the way of boobs. She was gently sliding her miniskirt higher on her thighs, giving me peeks at her panties. Libby was sliding her top lower, so I had a delicious view of her cleavage. Molly was moving seductively to the music that was playing in the background.

It was working. I could feel myself getting more and more excited. Brianna glanced up to see what was going on and saw what the three girls were doing. She quietly moved behind Bridget. Bridget did not notice, as she was focusing all her attention on my reactions to her teasing. Suddenly Brianna grabbed both sides of Bridget’s skirt and pulled down. The miniskirt went all the way to the floor where it was tangled around Bridget’s ankles. Bridget’s reflex was to try to step, but her foot caught on her skirt and she tumbled to the floor. Brianna called for Molly and Libby to help and the three girls all jumped on top of Bridget. Within seconds they had her panties off as well. They dragged her over to the bar stool where I was stroking away and held her standing up as close to me as they could. Her top was pulled up to just below her bra, so that she was bare from there to the floor.

This gave me a great view of her pussy and my juices were now flowing full speed ahead. I could feel myself headed for climax. I started breathing hard and arched my back. When I shot, there was only one real wad. It hit Bridget just left of her navel and started running down her bare midriff. Whatever else I ejaculated just sort of dripped out of the end of my dick. I went flaccid immediately.

“Ooh!” Bridget complained. “I didn’t deserve that.”

“No, but it was fun,” retorted Brianna.

[Memories for Life]

Another excellent continuation. The more I read, the more I want Brianna's payback to be a "living hell". She needs to be whipped naked in public and her exposed body available to any random male to happens by!

[HHHobo]

Stay tuned! You'll see that even Brianna has a human side.

[HHHobo]

Calm was restored, I got redressed in the same outfit, and we adjourned to the kitchen for some lunch. As we finished eating, I heard a car pull in the driveway. It was my sister Karen. I guessed she was providing transportation to the mall. It would take two trips to get us all there. Naturally I was in the first group, so I could be on display that much longer.

The mall was much like the time I went there with Libby. Brian disappeared to do his thing, probably in the computer store. When everyone got there, we started visiting every girly shop we could. We went to clothing shops and they made me try on all sorts of outfits. They bought one for me that was definitely over the top. We went back to Victoria’s Secret and I had to buy more lingerie. We tried on all sorts of shoes, but didn’t buy any. The cosmetics counter drew us, and soon I had a bag of new makeup.

I handled all of this pretty well. It was easy to do some of these things that were mere repeats of what I had done before. Anticipating some of this, I had worried that I would get a boner. But the excessive masturbation kept my wilie in a shrunken condition.

We stayed at the mall until dinner time and ate at the food court. Of course, I made many trips getting food for the girls. Sitting nearby were some guys who looked a couple of years older than us. It sure looked like they wanted to hit on us. Eventually they did wander over. The leader walked directly up to me. Before he could say anything, Brianna’s tart tongue drove him off. They engaged in some verbal warfare, but it was clear to them that we weren’t interested in serving their desires.

Back at the house I was stripped down to bra and panties. I was now redecorated for the evening’s festivities. The wig I was wearing was restyled so that it had a braid on one side and about 10 mini-ponytails on the other. The studs came out of my ears. A big hoop went in my left ear and a long ribbon streamer went in the right. Freckles were drawn on the right side of my face. One of my front teeth was blacked out.

Then the group moved on to new clothing. A pink T-shirt was held up before me. On the front it said in dark blue letters “I Eat Anything – Watch Out Girls!”. On the back was written “Crisco Kid – Fat in the Can”, with an arrow pointing down toward the bottom where my butt would be when I put the shirt on. One sleeve was cut into little strips right up to the shoulder. The other sleeve had been cut off altogether. When I put it on, it was quite long, but a “window” had been cut out right in front of my navel.

Next came a skirt of sorts. It had obviously been made from an old pair of jeans. It had a very uneven length. On one side it reached nearly to my knees. On the other it barely covered the side strap of my thong. The bottom was extremely frayed. There were a number of holes that had been partly covered with pink patches, leaving little peek-a-boo holes in to my thighs. It was held up by a pink belt that had kittens on it.

That didn’t end it. For my left foot I got a pink flip-flop. For my right I got a baby blue Chuck Converse high top basketball shoe and a shredded knee high to wear under it. A tacky pink plastic ankle bracelet was added above the flip-flop. I was truly a sight. The girls’ cameras were clicking merrily away.

I was trundled back to Karen’s car. This time we played “Sardine” and all of us crammed into the car. She drove us off to a different mall and stopped in the drop-off lane. Brianna squeezed out and pulled me after her. We were joined by Molly and Bridget. The rest of the group stretched out in the car, happy to have more room.

Brianna handed me a pink purse. She explained, “Inside the purse you will find some money and a list of items to buy. You must buy them from at least five different stores. There is also a sealed envelope in the purse. Once you have bought all the items, open the envelope and follow the directions therein. Don’t look ahead of time. The three of us will be following and photographing you. If you cheat, it counts as a complaint and you lose. Any questions?”

I shook my head, accepted the purse, and started into the mall. Once inside I moved over to one side to be as unobtrusive as possible. Nevertheless, people were staring at me. I opened the purse. The list was lying right on top. It seemed to be a very random list of items with several associated with babies. Feeling very embarrassed I set about my task.

It took almost two hours to buy all the stuff. I was pretty loaded down. I had received hundreds of stares, many rude comments, and several embarrassing questions, which I simply ignored. I even had to talk to mall security. I told them it was an initiation and asked them if they wanted me to leave. Secretly I hoped they would throw me out. They just laughed and asked me not to create a disturbance. I nodded and found a bench to sit down to open the envelope. During this entire time I had only seen my supervisors a couple of times. They were doing a good job of staying out of sight. I had no idea what had happened to Rachel, Colleen, and Libby.

I tore open the envelope and pulled out the sheet of instructions. I read in Brianna’s handwriting the following:

“Go to the rental lockers and put all the stuff except the baby things in the locker. Be sure to put the money in the slot and take the key. Go to the nearest women’s room and go into a stall. Be sure that at least one of the stalls next to it is empty. After you go in, one of us will enter the empty stall. Take off all your clothes. YOU MUST BE COMPLETELY NAKED!!!!! Break the water balloons down the toilet. Wrap the key in your bra. Wrap all the clothes inside the T-shirt and pass it underneath the stall to one of us. We’ll pick up the other stuff from the locker. Then put on an adult diaper. Put on the bib and the baby bonnet. Put the pacifier in your mouth and hold the rattle in your hand. You may leave the rest of the adult diapers behind. Now, leave the stall and the women’s room. You’ll have to be careful, because it will be obvious you are a guy, albeit a really strange guy. Your task is to find Karen. She will be parked at one of the mall entrances, but we’re not saying which one. You have to keep looking until you find her.”

It was all I could do not to groan or express some emotion. But I knew Brianna would be in a place she could observe me. She would certainly judge that to be a complaint. I gulped and set off. The first part was relatively easy. I found the lockers and checked a lot of my load. It was a relief not to be carrying so much shit, but I was really scared of what was next. In the times I had crossdressed before, I had only used the women’s room once. As I walked along, I noticed my reflection in the windows of the stores. I definitely looked female and very weird. I shouldn’t have any trouble getting in. It was getting out that was the problem.

I spotted the sign for the rest rooms and went straight for them. It did feel strange going in by the female sign, but I forged ahead. I checked out the stalls, slowing down, so that whoever was tailing me would see where I went. The end two stalls on the right were empty. I went in the second-to-last one. Within seconds I heard the door of the one next door close shut. “Willie!” I recognized Brianna’s whisper. “When you’re ready, shove it under the divider near the toilet end.” With ever increasing fear, I stripped myself of every shred of clothing, put the key in the bra, all of the clothes in the shirt, and pushed it under to Brianna. She grabbed it immediately. “Good Luck!” I heard her whisper, and then a little bit of a giggle. The adjacent door opened and closed.

Now I was so nervous I was having trouble getting my hands to work. It seemed to take forever to get the diaper fixed in place so that it wouldn’t fall off. With the tiny bonnet and bib in place, I felt like a total fool. I slipped the pacifier in my mouth and held the rattle in my hand. Now I sat and listened intently. I could hear activity in the room. A faucet was turned on and off. A couple of women were conversing quietly. I was hoping I could get a brief amount of time with the room empty, so I could make a dash for it.

Every time I thought I had a chance, I would hear the door open and someone new would come in. I was beginning to despair of ever getting a chance. I had no watch on, so I had no clue how much time was passing. Finally I heard a woman leave and silence descended on the rest room. I took a chance and dashed out. I sprinted for the door and flew into the hallway. A woman had been just reaching for the door handle. She stepped back in disbelief and stared at me. I didn’t pause for a second. I ran as hard as I could into the center part of the mall and searched for the nearest exit. I spotted it and made a beeline for it. I was hoping against hope that Karen would be parked outside the exit. No such luck! Her car was nowhere in sight.

I had to choose left or right to continue my search. For no real reason I went left. There was no sign of her at the next exit. It was dark out, but that didn’t mean that people didn’t see me. I was afraid of running into mall security. But I had no choice but to keep going. The mall has six exits. When Karen wasn’t at the fifth exit, I knew she had to be at the sixth. Just my luck I turned the wrong way when I came out. But when I got to the sixth exit, she wasn’t there either. Now I was totally panic stricken. I decided to reverse direction. I circled the mall again without seeing her. Now I was not only frightened, but I was running out of breath. I stopped to gather my bearings. I turned to look behind me and saw Karen drive up in her SUV filled with laughing girls. They pulled up next to me and pulled me into the car.

I soon learned what they had done. They figured I would go to the nearest exit from the mall. Brianna hid in a corner there with her cell phone. Karen was parked on the opposite side of the mall. As soon as I turned left, Brianna told Karen and she told Karen which way to go. The other girls were at the other exits and they all kept in touch so that Karen could always stay on the opposite side of the mall from me. They wanted me to go around the mall in my baby costume at least twice.