Cassandra & Carolyn

Cassandra and I had only been together for less than a month. You know how it is. Those first few weeks of wild, crazy love when you can’t get enough of one another. We were both eighteen and sex was still a new, forbidden thing of wonder. Our bodies were each, for the other, like untested carnival rides. We fucked a lot. I mean, a lot. My Dad worked days and her Mom worked nights, so there was always a place we could go. If, by some fluke, both our parents were home, we would go for long drives to secluded spots. Either that or over to my friend Greg’s house. He had a pool and a hot tub, as well as a well-stocked bar and perpetually absent parents.

Jesus, we did it until we simply couldn’t do it anymore. Luckily, at eighteen, I got hard-ons about seven times a day. Believe me when I tell you that not many of them went to waste. I must have spent a couple hundred dollars on condoms and, if we ever found ourselves without, we’d simply suck each other off. We both had oral fixations, thank God.

And after, or I should say in between, the sex, we would talk. I wanted to know everything about her and she wanted to know everything about me, but mostly we talked about sex.

Her sexual past was a lot more varied and interesting than mine, to say the least. Cassandra had taken my virginity and, prior to that, my only other experience had been lots of ball-busting foreplay with my frigid ex, Melissa. My hand-job stories were pretty boring in the face of some of Cassandra’s exploits. Some guys, I know, are intimidated by girls with a wild past, but I was never less than enthralled.

“I was kind of a slut,” she admitted sheepishly.

She told me about the time she and her two friends went to a motel room with two older guys. (Three girls and two guys meant Cassandra ended up sharing with a friend.) Then there was her three-way with identical twin brothers. (“Even their cocks looked alike.”) Or the time she jerked off a complete stranger in a crowded movie theater. Or the time when she, on a dare, went shopping for shoes in a short skirt and no panties so she could flash the salesman. An anal sex experiment using honey as a lubricant (“That was kind of messy.”) A wild summer at church camp, of all places, where she slept with five guys in less than two weeks.

“What’s the craziest thing you ever did?” I asked her once. We were in the shower together, following an entire morning spent screwing. We were both spent, and a little sore, but I knew the answer to this question could get the batteries charged again real quick.

Cassandra frowned, though. “I’m not ready to tell you that one yet. But I’ll tell you the second craziest.”

“OK,” I nodded, my imagination already going wild. “What was his name?”

“Carolyn.”

I nearly dropped the soap. “Carolyn? You did it with a girl?”

“Yeah,” Cassandra laughed. “That’s not that weird.”

Despite the two times I’d already gotten off that day, I was instantly hard again.

“What is it with guys and lesbian sex?” Cassandra asked, smiling down at my sudden boner. She soaped up her hand and started giving me a very in-depth cleaning. “I mean, what’s the big deal?”

“I don’t know,” I said, my voice shaking. “Please tell me about it, though.”

She laughed again and gave me a long kiss. “All right, but let’s go back into the bedroom.”

We rinsed and toweled off and climbed naked back into my bed. Just the thought, the bare mention, of Cassandra having been with a girl, had got me excited and ready again. I was wild with lust, kissing and nibbling her all over.

“Stop,” she said, pushing me off. “Do you want to hear the story or not?”

“Oh God yes please,” I gasped.

“OK,” she said patiently. “But you can’t touch me until I’m done. All right?”

“I’ll TRY not to,” I said, which was the best I could promise.

“This was at my old school,” she began. “Carolyn was in a few of my classes, and she had a reputation for being gay. But, the thing was, she wouldn’t admit to it. In fact, she was always going on about how much she hated dykes. If there was another girl who she thought was a lesbian, she would stalk and torment her. Literally. But she was so obsessed with the subject that it was obvious to everyone what was really going on. Everyone except her, maybe.”

“What did she look like?” I asked.

“She was pretty, in a way,” Cassandra said. “But, you know how the kind of butch-looking lesbians look OK because they’re, I don’t know, natural? Well, Carolyn wasn’t natural at all. She tried to dress like the rest of the girls, and do her hair and her make-up, but she just didn’t have a knack for it. It always looked really weird on her. Somebody trying hard to look normal, when she really wasn’t. So she didn’t really have a lot of friends, and neither did I.”

“Really?” I asked. I would have thought that Cassandra, as cool as she was, would have been incredibly popular.

“Well, that’s sort of the drawback to being . . . how I was. Girls hated me because I put out so easily and guys would maybe go out with me once or twice, but they didn’t really want to have much to do with me at school.”

“That’s terrible,” I said, taking one of her nipples tenderly in my mouth.

“Yeah, whatever,” Cassandra said. “I’m trying to tell a story here.”

“Keep going.”

“So, anyway, Carolyn and I started hanging out. She was funny and smart, a little obnoxious sometimes, and she could get abrasive, but she was OK to hang with. But the whole time I’m thinking about going to bed with her. I mean, she had this reputation, and I was wildly curious about it.”

“You were?”

“Yeah. My Dad had this secret cache of porno magazines. I knew where he hid them, and I’d look at them every chance I got. The stuff that turned me on the most were the pictures or the stories with girls having sex with other girls. God, it got me hot. Whenever I masturbated, that’s all I’d think about. Another girl. I’d even . . .” Cassandra laughed. “This is kinda weird.”

“What?”

“Sometimes, I’d play with myself until I got really, really wet,” Cassandra began to demonstrate, her hand reaching down between her legs. “Then I’d work my hand in as far as I could . . .” Four fingers disappeared inside her. “Then I’d lick my fingers to taste myself.” Cassandra thrust her hand into her mouth and started to suck it clean. It just about blew my mind.

“I loved the taste,” she said.

“So do I,” I said, and began to dive down to drink straight from the well.

Cassandra stopped me, though. “If you start that, I won’t be able to finish the story.”

I almost didn’t care, I wanted her so badly. But, I did want to hear the story, so I contented myself with helping Cassandra clean her fingers.

“Where was I?” she said.

“You were hanging out with Carolyn, trying to get her into bed.”

“Oh yeah,” Cassandra said. “It was rough at first, though. She still kept up with the ‘dykes make me sick’ stuff. I’d say things like, ‘I don’t think it’s a bad thing,’ and even ‘I’ve wondered about it sometimes,’ just to let her know where I stood, but she still kept on with it.”

“So then one night, she asked if she could stay over at my house. I was like, now maybe we’ll get somewhere. So we were up in my room, it was late at night, and I kind of gradually steered the conversation around to sex.”

“I’ll bet you did.”

“I told her all my stories, all the ones I’ve told you. I could tell by the things that she asked me that she didn’t have any experience at all. She was especially horrified when I told her about giving head. She was like, ‘You put his thing . . . in your MOUTH?’ and ‘When his stuff comes out . . . you SWALLOW it?’ She acted like she was really grossed out, but I could tell it was turning her on.”

“So then I hauled out my Dad’s magazines and we started to look at them together. I let her turn the pages, and she really lingered on the lesbian stuff. Carolyn would make comments about how disgusting it was, but it wasn’t even halfway convincing anymore. We were sitting really close, so close that I could feel her shaking with excitement. I don’t have to tell you how turned on I was.”

“Then she put the magazine down and said, all wistful like, ‘I’ll never get a boyfriend.’ And I said, ‘Why do you say that?’ And she said, ‘Because I’m so ugly.’ And I said, ‘I think you’re gorgeous,’ because right at that moment, she was. She was all flushed and trembling, aroused and terrified at the same time. She said, ‘I’ve never even kissed a boy. I wouldn’t even know how.’ So of course I said, ‘You can practice on me if you want to.’”

“She kissed me. And it was like I’d never kissed anybody before, it was so fresh and soft and new. We were both shaking all over. We kissed for a long time, then I took a chance and reached up and touched her breast. She was wearing a t-shirt and a bra underneath, but I could still feel how hard her nipple was through all of that. She let me touch her there for few seconds, then she pulled away.”

“She said, ‘I’m tired now. I want to go to sleep.’ So I stretched out on the bed and said. ‘All right. Let’s go to bed.’ But then she got up and grabbed the sleeping bag she’d brought over and spread it out on the floor. I couldn’t believe it. I said, ‘Why don’t you sleep in the bed with me? It’s more comfortable than the floor.’ But Carolyn just said, ‘No, that’s all right. I’m fine.’ Then she climbed into the sleeping bag without even taking her clothes off, and said, ‘good night.’”

“I was kind of pissed. She’d got me all worked up, and then just chickened out. So I said, ‘How can you sleep with your clothes on like that? I usually sleep naked.’ Then I stood up and took everything off, real slow so she’d have to watch.”

“You didn’t,” I laughed.

“Of course I did. I was taunting her a little bit. She didn’t take her eyes off me for a second, but all she said was, ‘You should really shave your armpits. That’s gross.’”

“It is not,” I said, kissing the soft clean hair under Cassandra’s arms.

“I got back into bed and turned out the light. I was so keyed up that I knew I’d never be able to sleep unless I got myself off, so I did it right there. I didn’t even try to be quiet about it, either. I didn’t care if she heard me. When I was done, I just rolled over and went to sleep.”

“I know there’s more to this story,” I said.

“Be patient, darling,” Cassandra said. “So I don’t know how long I’d been asleep, maybe a couple of hours. I woke up because I was cold. I opened my eyes and saw Carolyn standing beside the bed. She’d pulled the sheets off me. The closet light was on, and she’d opened the door enough so the light shined on my body without shining on my face. I squinted my eyes down so she wouldn’t be able to tell I was awake. She was in shadow, but it was obvious that she was naked from the waist down and that she had her hand between her legs, masturbating while she watched me sleep.”

“Oh my God,” I said. “Didn’t that freak you out?”

Cassandra smiled. “No. I kind of liked it. She stepped closer to the bed and her hand started moving faster. I could hear how wet she was. I could even smell her. Then she . . .” Here Cassandra laughed and shook her head. “Then she took her hand out and touched my lips really lightly, letting the juice just drip from her fingers into my mouth.”

“Jesus.”

“Yeah,” Cassandra said. “It was all I could do not to move or make a sound. But I knew that would ruin it. The only way Carolyn was going to do anything was if I pretended to be asleep. She ran her hand down my entire body, so lightly that I couldn’t tell if she was really touching me or if I was just feeling the heat of her fingers. My neck, my breasts, my stomach, then between my legs; so gently that it was barely a touch.”

“I had been sleeping on my side, but then I rolled over onto my back. I was still playing like I was asleep, like it was just by a happy coincidence that I ended up laying there with my legs spread open so she could get at me.”

“She stopped touching me and crawled onto the bed slowly, I can’t even tell you how slowly, creeping up between my legs so slow that she didn’t even make the bedsprings creak. Then I felt her mouth on me.”

Cassandra was breathless, lost in the memory.

“She did it so lightly, so gently,” Cassandra took my hand and demonstrated, her tongue fluttering on my palm so delicately it felt like a butterfly had landed there. “I didn’t think it could possibly get me off, but . . .” Cassandra now guided my hand between her legs. I tried to my touch as gentle as Carolyn’s. “She did it for so long. It felt like hours, just slow and light and persistent. I drifted in and out of sleep, for real, and every time I woke up, she was still at it and I was a little closer. I thought the sun would come up before I would, but when I finally got there, it was so intense. I couldn’t believe it. I’d never come so hard in my life, before or since. I cried out. I almost screamed. Carolyn froze. She just stopped. I couldn’t stand it, so I grabbed her by the hair and just ground her face into me. Then she went wild, sucking and licking and kissing. My God, I nearly passed out.”

“So I’m lying there, recovering, and Carolyn started to slip out of the bed. But I said, ‘Wait.’ That was the only word either of us spoke through this whole thing. ‘Wait.’ Because I had to eat her pussy. I just had to. That was the one thing I’d fantasized about most when I thought about being with another girl. Sometimes, with those magazines, I would actually lick the close-up pictures of all those cunts. I’d actually lick the magazine page. And I knew that this was a one-time deal. In the morning, it would be over, so this was my only chance for God knows how long.”

“Carolyn knew what I wanted. She climbed up onto the bed and spread her legs open and then she pretended to go to sleep. It was pretty obvious that we were both awake, but it was like that was the only way she could bring herself to do anything. So whatever. I was beyond caring. I didn’t have the patience to do to her what she’d done to me, so I just dove in there. I went straight for her clit. It was weird, it was so swollen and hard that it was like a little nipple.”

“The other weird thing was how different she tasted from me. She was almost sweet. I loved it. I couldn’t get enough. I sucked and licked and she got off hard and fast. She started to twitch and spasm and she got so wet all of the sudden and I just drank it all up.”

“Then she pushed me away. We didn’t say another word. She climbed out of bed and crawled back into her sleeping bag. I got back under the covers, and we both just went to sleep.”

“The next morning, while we were eating breakfast downstairs, she looked at me and said, ‘I had the weirdest dream last night. I dreamed that we fucked.’ ‘Really?’ I said. ‘Yeah,’ she said, ‘Then I woke up and I almost puked.’”

“No,” I groaned.

Cassandra nodded sadly. “Yeah. One of the most amazing experiences in my entire life, and that was all she could say about it. She couldn’t even admit that it really happened.”

“Then, back at school, she started telling everybody that I’d made a pass at her. Nobody believed her, really, but it didn’t matter. That was the end of our friendship.”

“She graduated a year ahead of me,” Cassandra went on. “She went right into the Army after school and, sort of ironically, that’s where she finally came out. I got a letter from her when she was stationed in Germany, and she apologized for how she’d treated me and she told me how much the night we’d spent together really meant to her. She had a German girlfriend and, she wrote, ‘She has hairy armpits just like you!’ But I never heard from her after that.”

“Wow,” I said. It seemed like all I could say. “Wow.”

Cassandra looked up at me and smiled. There were no more words to be said. I rolled on top of her and we made love. Slowly at first, but gradually becoming more and more frenzied. I couldn’t get the images from her story out of my head. It excited me so much, more than anything she’d ever told me before. I’m not even sure why. Just that she’d done this incredible, forbidden thing and then allowed me inside. It was like making love to a Goddess. She was turned on by having told the story, too. I could tell. She was on fire, wild and alive underneath me, receiving me as I crashed down on her like hurricane waves.

When it was over, we were spent. Completely. There was no energy left in either of us and we just lay there naked and sweaty in each other’s arms. That’s when I remembered something she had said.

“Wait a minute,” I said. “That was the SECOND craziest thing?”