Chapter 66: A Night to Remember

Originally posted on: Mon Feb 05, 2007 5:27 pm

Prom night was one week before graduation. The four of us; Tim and Cindy, Angie and me, doubled for dinner and then headed for the big party. The night before I had a long talk with my dad and he set up a room for me at one of the hotels that we 'worked' for. I explained that I didn't have any expectations but that I didn't think that was a good excuse for not planning ahead anyway. If something was going to happen between Angela and I there was a good chance it would be this night. He didn't understand how Allison and I could be okay with all this but he went along anyway. He booked us a two room suite. Thanks Dad.

The dance was the bomb! Tim and I both rented tuxedos. Mine was the traditional black; his was a dark blue over a lighter blue shirt that was the exact shade of his eyes. I made a note to be a little more flexible in my formal attire in the future. The girls? You know women and a chance to dress up... They were spectacular! Cindy has what some call dirty blonde hair; it's too dark to be blonde but not really dark enough to be brown. And she has hazel eyes. She was wearing a deep green dress, with lighter green trim; the dress really brought out the green in her eyes; to the point that the brown almost disappeared. I wondered if maybe she had helped Tim pick out his shirt.

As good as Cindy looked, she paled in comparison to Angela. Stunning, absolutely stunning; her dress was a deep plum and she had worn her hair down straight. I realized later that she did that so I wouldn't look like a midget standing next to her. I don't know what they did to her hair but it seemed to catch every ray of light. Highlights danced up and down the length of it every time she moved, and she moved a lot. We had only managed to take three dance lessons together but it really helped to ease my natural intimidation level and keep me from feeling and looking like, well, a kid.

There was one tense moment when Roger Elliott came over to our table. I was afraid it was going to get ugly but he said he just came by to apologize for the whole thing at the mall and to make sure I knew that he had no hard feelings about it. He said he deserved to get his ass kicked for even being a part of it. We shook hands and he went back to his date.

Cindy was all over Tim. I thought she was going to start tearing his clothes off on the dance floor when the music slowed down. When it started looking dangerous I cut in and danced with her for a few songs. Tim danced with Angela and while everything looked proper and normal; they both had dates after all, I knew that it was a special time for them. Afterward while I was dancing a slow song with Angela again, I suggested that maybe we better think about leaving before anyone got arrested.

"No kidding, Jimmy, that girl is some kind of horny right now. I've never seen her like this. I mean, I've known her for years and I know she likes a good fuck as much as anyone but I've never seen her like this. She's got it bad. I'm a little afraid she might do him in the back seat with us watching."

"If we don't get her out of here, she's liable to do him under the table." I glanced over at them. "Or on top of it."

"There is that. I guess we could find someplace to park and you and I could go for a walk or something."

"I have a room reserved at the Suites."

She stopped dancing, pulled back, and looked at me. "You do?"

I pressed just enough to remind her where we were and what we were supposed to be doing. Once we were moving again I answered, "Angela, before you say anything let me make something clear. I have no plans and no expectations, but I thought it might be best to be sure that if things went that way we weren't going to have a problem with locations. It's a two room suite so there's room for all four of us if we need it."

"You never cease to amaze me, Jimmy." She looked past me to where Tim and Cindy were dancing. "She's trying to chew the buttons off his shirt. Not a good sign. I think it's time we took a trip to the ladies room. You talk to Tim." She kissed me on the cheek and we headed over to break up the floor show. Angela whispered something to Cindy and they headed for the ladies room. Tim and I headed back to our table.

"How are you holding up?" I asked.

"I think I'm going to sprain something. I feel like I've got a tree in my pants and I'm afraid everyone is staring. It's not that bad most of the time but when the music slows down and she starts humping my leg on the dance floor..."

"How would you feel about maybe moving to a more private venue?"

"What do you mean?"

I explained about the room.

"You're an amazing guy, Matthews. You should give lessons, write books, or something. I know you; you weren't expecting or anticipating, you got the room just in case didn't you?"

"Pretty much, yeah. Angela made it pretty plain some time ago that she wanted my body. I've discovered that once a girl makes up her mind it's really just a matter of when, not if, it's going to happen. If it was going to be tonight I wanted it to be someplace nice."

The girls were threading their way back through the crowd toward us. We gathered up our stuff and headed for the door. In the interest of safety we put Cindy up front with Angela.

When we got to the hotel, I was going to go in alone to get the keys but Angela just laughed and said, "Don't worry about it; it's prom night and everybody knows exactly what's going on."

So we all strolled into the lobby together. Cindy was managing to behave herself now that it appeared she was going to get what she wanted.

"Reservation for Matthews," I said as I reached the desk. I handed her my license for identification.

The girl behind the desk looked like she was probably in college, she just grinned as she pulled the information up in the computer. "Yes, Mr. Matthews, we have you in one of our salon suites. Enjoy your stay." She handed me two electronic key cards.

"Thank you. How late is the kitchen open, and what time do they open the restaurant for breakfast?"

"We begin seating for breakfast at 5:30. The full menu is available until 10:30 PM and there is a late night section available 24 hours a day. Menus are in your room."

"Thank you," I looked at her name badge, "Abbie."

"My pleasure, sir. Enjoy your stay."

Our room was on the tenth floor, the double doors off the plush hallway were the first clue that my dad had gone all out. The doors opened onto a seating area that was very nicely furnished with two love seats, tables, reading lamps, a desk, and over to one side a full table with four chairs. It wasn't a two room suite; it was a two bedroom suite with the bedrooms on opposite ends of the living area. I recalled our path and the general layout and realized that this room took up one whole end of the floor. I checked the drapes and found a breathtaking view of the city laid out below us.

"Wow," said Angela as she joined me at the window. "Timmy, you gotta see this."

There was no answer and when we turned to check on them we found Cindy had pushed him up against the closed doors and pinned him there with her tongue. Not being stupid he was making no real effort to escape. I checked Angela's face to see her reaction and found a strange combination of, joy, sadness, and lust. I took her hand and squeezed it to let her know I understood what she was feeling. I sometimes felt it when Allison and Shannon were together. Joy that they were happy, sadness that they were happy without you, and lust because you wanted to join them. As we stood watching, Cindy began backing into the seating area, pulling Tim with her as she came. Tim was kind of looking past her head and guiding her around the furniture. When she was in the middle of the two love seats she turned ninety degrees, broke the kiss, dropped to her knees, and started undoing his pants. Tim looked appropriately stunned.

"I think that's our cue, Jimmy," Angela said. "Come on."

Cindy stopped what she was doing and turned to us, "No, don't go." She looked at Angela. "I want you to watch me fuck your brother. It'll be so hot!"

"You're serious?" Angela asked.

"Oh God yes!" Cindy said. "I want to do everything. I want to make this a night we never forget; I want to suck his cock while you watch, then I want to ride him till he explodes. Later I want them both to fuck me at the same time; if you don't mind that is. It's a fantasy of mine and I finally have the chance to do it. And some time before we go home, I want to eat your pussy."

Angela's eyes got huge. "Really? I didn't know you liked girls."

"Yes, really; God this is like a dream come true. I never thought I'd get a chance like this. I don't know if I like girls but think I might, and I know you've been with girls before, well, one at least, so I want to try it. I want to take advantage of this moment. I may never get a chance like this again. Please?"

Angela looked at me to see what I was thinking; I just shrugged, then moved behind her and unzipped her dress.

"What about me?" Tim asked. "Don't I get a say in this?"

There was an echo as we all answered at the same time, "No."

He just smiled. "Just checking." He shrugged out of his jacket and Cindy started untying his shoes so she could get his pants off. I couldn't help but smile when I saw that Angela was wearing the exact set of underclothes that she had shown me in Victoria's Secret on our first date, way back before Christmas. They were plum satin to match the dress, with black lace trim. The thigh high stockings she wore were trimmed to match. She gave me a wink and a smile when she saw that I recognized them. That pretty well confirmed that while I may not have had plans or expectations for this night, she certainly had. The best part was I got to take them off bit by bit as the night progressed. Except the stockings, when she eventually lost the rest Tim and I both decided she looked too hot in the stockings to just cast them aside without a really good reason.

It was a very long night as we helped Cindy live out all of her fantasies. Tim and I sat on the love seats and the two girls took turns demonstrating their different oral techniques. Apparently Cindy had figured out where Angela had been getting her itch scratched all these months. She didn't have a problem with it and admitted that her first time had been with her cousin and the two of them still humped like bunnies any time they were together. I thought Tim was going to die when the girls teamed up and began sharing his cock. It brought back fond memories of the first time Allison and Shannon had French kissed around the head of mine. The kiss grew all on its own, and soon Tim was forgotten as Angela slowly shifting her position: she pulled slowly away from the kiss and Cindy followed her, trying to keep the contact as Angela rolled down onto her back. Then she sat up and let Angela draw her into position over her mouth. Angela demonstrated the value of experience and as Cindy's orgasm drew close I stepped in front of her and she took me into her mouth. She reached with her other hand and Tim moved to stand on the other side of her. She went back and forth until Angela took her over the edge in a wrenching orgasm. As soon as she recovered she indicated that she wanted Tim on the floor in front of her and me fucking her from behind while she finished him off.

"Okay, forgive me for being the voice of sanity here but maybe we should move to one of the bedrooms before we all get terminal rug burn." I suggested.

As soon as I mentioned it she looked at her knees and saw that they were already red from kneeling over Angela.

"Ooh, yeah that's probably a good idea. Oh, and I've got to call my mom and tell her I won't be home."

"Good point," Angie said.

When I asked if her parents were going to be okay with it I found out that she was an only child and had been raised solely by her mother. Her mom respected and trusted her enough to make adult decisions about adult issues. Angela just shook her head and said she wished her mom could be so enlightened in her approach.

Cindy called her mom and told her where she was and not to worry or wait up. Then Angie called her folks and told them that we were all going to a private party at one of the local hotels. I guess her mom said something because Angie got a little irritated when she answered.

"What, Mother, you think I'm taking him to an orgy or something? Don't worry; we'll be fine. We'll see you in the morning. Yeah, love you too. Good night." She hung up the phone and Cindy took her hand and started leading her toward the bedroom with Tim close behind.

I held back just long enough to call down to the kitchen and order some snacks; nothing fancy; just two orders of hot wings and a vegetable plate. The voice on the phone said that it would be about thirty minutes and that they would just leave it in the entryway.

By the time I joined them in the bedroom Angela was taking a turn on Cindy's face while Tim watched. I closed the doors behind me, moved to the open side of the bed and began licking Cindy. She gave a startled gasp at the sudden assault then dove back into her chosen task with new energy. Tim moved in front of his sister and now everyone had something to do.

We broke for snacks some time later. Resting and regaining energy. Cindy was one of those girls that peaked quickly and often. She had at least one orgasm for each of ours. She came the hardest when I suggested we try Allison's trick of putting the girls into a sixty nine position, I fucked her while Angela ate her around me. Tim was resting at the time.

After we had finished with the food Cindy took the left over ranch dressing and began finger-painting trails on all of us. This led to another tongue party and everyone got back in the mood quickly. This time it was Angela on her back under Cindy, with Tim between her legs and me in Cindy's mouth. Again, Cindy came twice before I finally released my load into her mouth.

Both girls were on the pill but we had been using condoms for any penetration other than oral. Cindy had brought a twelve pack with her and we had gone through a little over half, when she said there was one more thing she wanted to try. Tim had regained his strength by now and she took him into her mouth a few times, then unrolled another latex over his length.

"I want you to fuck my ass," she said.

"Won't that hurt?" Tim asked.

"Probably at first," she answered. "That's why it gets to be you. You're longer but he's thicker and I think I'd rather not risk it the first time."

"Let me help you get ready," Angela offered.

Cindy just smiled and said, "There's a small bottle of oil in my purse."

Angela retrieved the oil and positioned Cindy on all fours and began dripping the oil on and around her little pink rosebud, rubbing it in with a finger as she went. By the time the area was liberally coated Cindy was starting to relax to the sensations. Angel dripped some extra oil on her finger pressed it inside the girl's opening. You could see Cindy tense again at the invasion but she let out a long sigh at the same time.

"Umm, that feels good. More."

Angela added more oil and soon had her finger all the way in. Then it was her thumb and she pumped it in and out until the ring of muscle had completely relaxed. Cindy was breathing hard and humping back against her hand by now.

"Now," Cindy said. "Oh God, fuck me now."

Tim and I were both standing at full attention just from watching all this. Angie moved aside and Tim moved into position. Angling down he positioned himself at her opening and pressed forward slowly. Good thing she'd bought lubricated condoms. Angela's ministrations had done their job and she opened smoothly to his advance. Cindy's head snapped up and she gasped as the head popped through her outer ring.

"Oh yeah," she panted. "Oh god, more." Her hands balled into fists, bunching up the sheet as he pressed himself deep inside her. Soon Tim was balls deep and she was writhing on the mattress, face and chest pressed to the sheets with her ass arched high in the air. I couldn't believe she had just had an orgasm from the first insertion. But the look on Tim's face confirmed that those were very real spasms he was feeling. He looked like he was about to explode. As Cindy recovered and relaxed, you could see from his face that the crisis was passing. "Now fuck me;" she said. "Fuck me hard; take me, make me your bitch; pull my hair and fuck me 'til I can't walk."

I thought she was kidding but she pressed herself back up to all fours and flipped her head so her hair trailed down her back. Tim gently took her hair into one hand and began sliding slowly in and out of her.

"No! Harder. Hurt me, show me that I'm yours." She pulled her head down so her hair was taught in his grip.

He got the idea and jerked her head back as he drove hard into her.

"Yes, oh god yes, fuck me harder, hurt me."

All hesitation disappeared as Tim reached up with his other hand to grip her hair harder and began slamming into her for all he was worth.

"That looks like fun," Angela said, motioning me over and climbing up onto all fours next to her girlfriend. "Not my ass, but fuck me like that." I reached for a fresh condom but she stopped me, "No, I'm safe and I know where you've been. I want to feel you come inside me."