Cassandra and Annie Ch. 01

Cassandra and I had been together for three months, but it seemed much longer than that. Things were so intense with that girl. Three months and we were already talking marriage and babies and the rest of our lives and it didn't seem that far-fetched. We'd progressed beyond our initial "crazed sex bunnies" stage and were moving into deeper waters. The sex was still amazing, but it had become more relaxed, less desperate. Since she'd confessed to me her most shameful secret, an affair she'd had with her own brother (see "Cassandra's Secret") the sex between us had become less scary/intense, and more warm and intimate. Not as frequent, from twice a day to three times a week, but I still couldn't complain.

We were both taking day classes at a local community college. That plus the fact that we both had part-time jobs now (she was waiting tables, I was working at a record store in the mall) meant that we were no longer together every minute of every day as we had been practically all summer. I spent most nights at her house, though. Her Mom was surprisingly cool about this. She liked me and I think she understood that we were serious about one another.

So that's where we were at when Cassandra's friend Annie came to stay with her for a week. They'd been best friends at Cassandra's old school before she'd moved here. Cassandra talked about her a lot, but this was the first time I'd actually met her.

Annie was an outwardly very shy and quiet person, but she had a crazy streak in her just as Cassandra did. I swear those two brought out the worst in each other. They'd dare each other to, say, shoplift from the mall, or to walk into a hotel and swim naked in the swimming pool. Annie had light brown hair, was pretty, a bit heavier than Cassandra but by no means fat. I thought she was attractive, but at first I followed what I believed was a very sane policy of not paying too much attention to my girlfriend's friends.

We even tried to set her up with my friend Jerry while she was in town, but it became clear pretty quickly that they weren't really into each other. Jerry was into punk and hard-core industrial music and Annie still thought Huey Lewis was kind of cool. At the age of nineteen, this was a serious cultural divide. Still, we went on a few double dates together.

Then, one night that week, I was sleeping over at Cassandra's. We had just made love and were lying there, holding one another and waiting for sleep. Cassandra rolled over and asked me, out of the blue, what I thought of Annie.

"She's pretty cool," I said.

"No," Cassandra said. "I mean, do you think she's sexy?"

I wasn't sure at all how to answer this question. Cassandra had not so far proven to be the jealous type, but I was still wary.

"I guess she's OK," I said, a pretty neutral reply.

"The reason I'm asking is," Cassandra leaned on one arm beside me on the bed. "Well, you know those Nancy Friday books my Mom has?"

I nodded. For those unfamiliar, Nancy Friday has written a series of books about female sexual fantasies. She examines the psychological and sociological significance of the fantasies, but of course everyone skips over those parts. The fantasies themselves are unbelievably hot. Every perverted thing you can think of. I highly recommend the books. Cassandra and I sometimes read passages aloud to get us in the mood. Never failed.

"Well," Cassandra said. "Today Annie was reading one of those books. A chapter about group sex, and she said, 'Wouldn't it be weird if you, me and Christian had a menage a trois?'"

I was literally stunned into silence.

"Christian?" Cassandra said after a while.

"Yeah, I'm here."

"We talked about it for a while. I said I'd ask you if you'd be into that."

"Are you kidding?"

"No," Cassandra said.

"You'd do that?"

"Sure," she said. "Why not?"

"I would have sex with Annie?"

"Yeah."

"And you wouldn't get jealous?"

"No," Cassandra said. "I'd be right there with you."

"So you'd have sex with her too?"

"That's what a menage a trois is." She said this very slowly, as if explaining it to a child. I know I was being dense, but I had a hard time believing that what I was hearing was true.

"Oh my God," was all I could bring myself to say.

"So, you're interested?"

"Of course I'm interested."

"OK," Cassandra said. She rolled over, her back to me, and yawned. "I'll tell Annie."

Even though we'd just had sex, Cassandra's surprising invitation had me at full mast again. I slid my hand between her buttocks, my fingers searching for moisture. She stiffened up and pulled away from my touch.

"Christ, we just did it," she said. "Come on, I'm tired."

So I just lay there beside her, thinking about what she'd said. It was a very long time before I could fall asleep.

The next day we already had plans to go into Chicago, forty miles away, with Annie and Jerry. The girls liked to check out the funky little thrift stores in the trendy gay neighborhoods, and Jerry and I liked going to the cool record stores. Four small-town kids in the big city.

Needless to say, I was seeing Annie in a completely new light. Like I said, I'd never looked at her too closely before, but now I couldn't keep my eyes off her. I discovered that she was extremely pretty, with big brown eyes which seemed to stay on me as much as mine were on her. I know this might be hard to believe, but that was the first time I noticed how nice her breasts were. I hadn't considered them before, but I saw now they were like big, fluffy pillows and I drove myself crazy wondering what it would be like to lay my head between them.

Part of the reason for this was that, in contrast to Cassandra, Annie dressed rather conservatively. Whereas Cassie favored things like short spaghetti–strap peasant dresses with nothing underneath, Annie always wore slacks and blouses buttoned to the neck. I knew rationally that she must have had a body beneath all that, but it took real focus to determine what that body might be like. Until today, I hadn't made the effort.

When we finally got back to town, I drove to Jerry's house and pulled up in front. I guess he took the hint, because he got out of the car without complaint. Annie got out to say good-bye and gave him a pretty chaste good-night kiss on the mouth. Weirdly, I felt a flush of jealousy.

Then she got back in the car and the three of us went back to Cassandra's. I was so hard in my jeans that it was difficult to shift gears.

At Cassie's house, we went straight to her room. None of us had said anything, but we all knew what was going to happen. I sat on the bed and Annie sat beside me. Seizing the initiative, I kissed her.

It was very strange, kissing this girl full on the mouth while my girlfriend watched from across the room. I think they were both surprised by my boldness in making this first move. Hell, I surprised myself.

"Well, you don't waste any time," Cassandra noted.

Annie pulled away. "You're a good kisser," she said.

"Cassie's better," I said.

Annie smiled. "I know."

Cassandra came over and sat down on the opposite side of Annie. She put her arm around her friend. "We were making out in the back seat for half the ride home. I'm surprised you didn't notice."

They then proceeded to demonstrate. A deep soul kiss with light friendly touching. It was amazing to behold.

"Wow," I said when they finished.

"Are you sure Jared won't mind you doing this with us?" Cassandra said, teasingly. Jared was Annie's boyfriend back home. They'd met at church camp and he was apparently very serious about sin and guilt. Annie had confided that they'd had lots of oral but had only actually had sex once, the first time for both of them. Of course, this meant Annie was practically a virgin.

"If I told Jared about this, his head would explode," Annie laughed. She kissed me again. From the other side, Cassandra nuzzled her neck and cupped Annie's fabulous breasts.

"He won't even come in my mouth," she said. "He's afraid to."

"What's he afraid of?" I said, my voice shaking, unable to rise above a whisper.

"Brimstone and hellfire," Annie laughed. She turned to Cassandra. "Do you let Christian come in your mouth?"

Cassandra kissed her again, mumbling an affirmative. "Mmm-hmm."

"Do you like it?" Annie said breathlessly.

"I love it," Cassandra said.

"Do you swallow it?"

"Mmmm," Cassandra answered. The girls kissed again. I held them both and just watched. Then I was kissing Annie again. It went back and forth like that for a little while, Annie kissing each of us in turn.

"I want to watch," she said after a while.

"Watch what?" I said.

"I want to watch her suck your cock." Annie was not typically one for vulgar talk. The word "cock" sounded blunt and outrageous when she said it.

"OK," Cassandra said, sliding off the bed. She kneeled on the floor before me and unzipped my jeans. I was hard as a railroad spike. She leaned forward and, smiling up at us, took me into her lips. Cassie was incredibly talented with her mouth, and it was made even more intense by how Annie watched with rapt fascination. She brushed her fingers along Cassandra's cheek, which bulged with my erection. I think Cassie was showing off a little, blowing me like a porn star, alternating between deep plunging and agonizingly slow tongue action on the head.

Annie kissed me, her mouth at my lips just as hungry as Cassandra's at my cock.

Finally, she said, "I want to try."

The girls traded places, Annie kneeling on the floor now and Cassandra sitting beside me on the bed again.

Annie regarded my penis with curiosity. "Don't come yet, OK?" she said. "Maybe later I'll want to try that, but right now I just want to suck you a little."

"OK," I mumbled. I was still shaking with excitement. Cassandra slid her arms around me as her best friend took me in her mouth.

Annie wasn't as skilled as Cassandra, but the very fact of her inexperience made it really hot. She was like an eager student, trying to imitate Cassie's cocksucking style. I leaned back in bed and Cassandra kissed me all over my face, her hands going wild all over my chest and arms.

"Having fun?" she whispered as she sucked my earlobe.

I could only nod. I was approaching the edge. I put my hand on Annie's head.

"You better stop," I said.

Annie released me and smiled up, clearly eager for my approval.

"Thank you," I said. "You're amazing."

All three of us got undressed then. Cassandra turned out the lights and lit some candles. She put on some music to cover any noise we might make. After all, her Mom was still awake.

We laid down naked on Cassandra's narrow twin bed, Annie between us. I had said that her breasts were wonderful, but that was when they had been contained within the industrial strength bra she wore. Now unfurled, glowing with the golden candlelight, they were nothing less than spectacular. Shimmering like tear drops, wine-colored nipples at stiff attention. Cassandra seemed as enchanted by her friend's breasts as I was. We each went after one, like hungry infant twins. In my mouth, Annie's nipple grew fatter and harder. It was almost like sucking a little cock.

My hand and Cassandra's hand each reached down between Annie's legs, crawling through the stiff wiry hair, racing to find her clitoris. Cassandra got there first and I felt Annie tense up with the pleasure. My fingers dipped down below and found her dripping wet.

"Go down on her," Cassandra commanded.

I didn't need to be told twice. I crawled down between her legs and took as much of her pulsing, dripping pussy into my mouth as I could. Cassandra's fingers were still at work down there, and I licked between them. Just as I had been amazed by how different Cassandra had tasted from my first girlfriend Melissa, I was amazed again by how different Annie tasted. Cassandra was wild and musky, like some exotic fruit. Annie was like sweet heady wine, dripping with Merlot. They received it differently, too. Cassandra always moved under my lips, squirming and bucking. Annie lay as still as she could, like she was afraid she would scare me away. Her body shivered, though. Little electrical tremors all up and down her legs. I glanced up and I saw that Cassandra and Annie were kissing and stroking each other's breasts.

After what felt like a very long time, Cassandra grabbed my hair and pulled me away.

"He does that well, doesn't he?" Cassandra said.

"God yeah," Annie gasped.

"But now it's my turn."

Cassandra dove into her friend's sweet pussy. There is nothing, and I mean nothing, in this wild wide world that compares to the sight of your girlfriend going down on another woman. Annie gasped, as if surprised. All I could do was watch, and stroke my cock helplessly. Annie looked over and saw that I what I was doing. She watched, frankly amazed, her jaw slack with the pleasure of what Cassandra was doing to her.

Cassandra raised her head, but Annie grabbed her and shoved her back down.

"Don't stop," she begged. "I'm so close!"

Cassandra, laughing, lapped furiously at Annie's clit until the girl was practically screaming. I stroked myself hard, forcing myself to stop just short of shooting off. I was throbbing, my cock buzzing.

Cassandra crawled up into Annie's arms. "Do you want to go down on me?" she asked.

Annie shook her head, disappointing me greatly. "Sorry," she said. "I'm just not ready for that."

Cassandra frowned, a bit disappointed also I think. "Well, what do you want to do?"

Annie looked at me, then whispered in Cassandra's ear. Cassandra nodded.

"She wants you to fuck her," she said to me.

I crawled over to her without hesitation, but Annie said, "Wait."

Annie grabbed her purse off the floor and pulled out a condom. "Would you put this on?"

"Sure," I said, already tearing it open.

I climbed on top. Cassandra grabbed my rubber-sheathed penis and guided it into her friend's pussy. Annie gasped and tensed up. She was wrapped around me unbelievably tight. I realized that she was scared, that maybe I was hurting her.

"Are you OK?" I whispered.

She nodded. "You're bigger than Jared, that's all."

"Relax," I said. "Kiss me."

Annie kissed me. I rolled in and out of her, slowly. Cassandra's hand still held me down there, as if she wanted to verify that I was in fact penetrating her friend. It was kind of strange. Annie had loosened up a little, but was laying still as a corpse. I couldn't feel much with the rubber on anyway, so after a few minutes I pulled out.

"I'm sorry," Annie said.

"Don't be sorry," I said. "You were great."

"Now what do you want to do?" Cassandra asked me.

"We can do anything?" I said.

"Anything Annie's up for," Cassandra smiled.

"I want you to get on top of me while Annie sits on my face," I said. I had given this some serious thought.

"Like a human pyramid?" Cassandra laughed.

"Yeah, a human pyramid."

So there was a few seconds of arranging limbs. Cassandra pulled off the condom and tossed it away with distaste. Then she straddled my lap, pulling me into her buttery softness.

"You don't use protection?" Annie asked, as she lowered her dripping vagina onto my eager mouth.

"I'm almost on my period, so it's OK," said Cassandra. "Besides, I hate those things."

Annie squirmed on my face. "Can you breath back there?" she asked.

"Mmm," I mumbled, my mouth full of her.

I was lost in ecstacy. This was the most incredible thing I'd ever experienced. Two wonderful vaginas. Cassandra was doing the circular rocking motions with her hips that she knew drove me crazy, flexing and unflexing her vaginal muscles around my cock. She was so hot, so wet. Annie was moving, too, lifting up off me to tease me, then sitting down fully so I was practically drowning in her. I bore the weight of the two women easily, they crushed me in a most pleasant manner. I couldn't see anything except Annie's cute ass, but I could tell by the way they were moving that the girls were kissing each other, their mouths forming the apex of the pyramid.

I gave Annie's asshole a little lick. Cassandra likes that, but it was clear that this made Annie uncomfortable. She tensed up and pulled away, so I contented myself with her delicious, wine-flavored pussy. I thrust my tongue deep inside, to penetrate her tight little hole. Then I sucked on her pearly clitoris. She squealed and squirmed above me.

I could tell by the way Cassandra moved that she was close. She was going faster, straight up-and-down plunging instead of her crazy circles. Her pussy squeezed me tight and I could feel it getting wetter. Both girls were moaning, their cries muffled by each other's lips. Annie suddenly filled my mouth with a spurt of fluid and I felt her pussy twitching and spasming over my lips. At the same time, Cassandra stopped riding me and just fell upon me with all her weight, burying me in her to the hilt. Her vagina pulsed like a heartbeat.

I had just got two women off simultaneously. I felt like Superman.

They both rolled off me, laughing breathlessly.

"You haven't come yet?" Cassandra said in disbelief.

I shrugged. It was true. Usually, I lasted at the longest fifteen or twenty minutes, but the three of us had been at it for almost an hour and I still had a rock-hard-on. I gave thanks to the God of Erections for this miracle.

"OK," Cassandra said, a bit impatiently. "How do you want to get off?"

I was debating in my head which girl I wanted to have suck me off when Annie said, "I want to watch him do it himself, with his hand."

We both looked at her curiously. "I've never seen a guy do that," she said. "I think it would be cool."

"Well, you heard her," Cassandra said.

So that's how, at the end of my first taste of group sex with two gorgeous women, I wound up jerking off.

I have to say, though, it was kind of exciting having them watch me. It didn't take long, either. Just a few minutes of fucking my fist and I was spurting all over the place. The first couple spasms were so powerful that I sprayed my own chin and chest. The next six or seven spat great puddles of semen all over my belly. It was a pretty intense ejaculation, I was so keyed up from the past hour, and I just lay there breathlessly, covered in come.

"Wow," Annie said. "That's a lot."

"Do you want to taste it?" Cassandra asked.

"No," Annie balked.

"Come on, you have to try it." Cassandra dipped her finger in my flooded naval and brought a sticky glob to Annie's lips.

Annie tasted it curiously. "Salty," she noted.

"I love it," Cassandra said.

Then, God bless her, she lapped at me like a kitten. She cleaned me up, licking away every drop. I don't know why this was so gratifying, but it blew my mind. When she was finished and gave me a salty kiss, I was even more in love with her than I had been before.

So that was my first three-way. The story does have a brief epilogue, though. A little later, Annie had fallen asleep and Cassandra was curled naked in my arms.

"Did you like that?" she asked sleepily.

"That was the most amazing thing that's ever happened to me," I said, with utter sincerity. "Thank you so much."

"Well," Cassandra looked up at me in the dark. "I did kind of have an ulterior motive."

"What do you mean?"

"That was one of your all-time fantasies, right?"

"Yeah, it was." There was no use denying that.

"I have a fantasy, too," Cassandra said.

"Oh, really?" I said. "What's your fantasy?"

"I want to be with two guys."

"I thought you already did that." I remembered a story she told me about an afternoon spent with twin brothers.

"Yeah, well, I want to be with two guys who . . ." her voice dropped to a whisper. " . . . do things to each other."

"Oh," I said, a bit taken aback to say the least. "Ah . . ."

"You told me you've thought about being with another guy."