tagGroup SexCassandra and Steve

Cassandra and Steve

byChristian Black©

All right. So, about a month and a half had passed since Cassandra and I had a three-way with her best friend Annie (see "Cassandra and Annie" for that story.) That was amazing, of course, but in hindsight I don't think it was worth what followed. Believe me when I tell you that the whole group sex thing, as tantalizing as it sounds, can be incredibly destructive if not handled right.

Cassandra, Annie and I all got together two more times, but neither of these encounters were as satisfying as the first. There was just too much going on emotionally for the sex to be as uninhibited and wild as that first incredible night we'd spent together. I began to have feelings for Annie, and I think the girls had some jealous resentment towards one another. They got competitive, which is not nearly as fun as it sounds.

A couple weeks later, Annie and I spent an afternoon in a cheap motel without Cassandra, and it felt like betrayal. The guilt undermined any pleasure I might have felt. (Cassandra and Annie got together a few times without me, but strangely I didn't really mind.) After that, Cassandra borrowed Annie's car and got into a little fender-bender accident. They would have just laughed about that before, but with all the weird tensions in the air, this provoked a screaming argument between the two girls which effectively ended their friendship. Of course, it also dissolved the triangle.

Things were strained between me and Cassandra after that, too. We quarreled frequently for the first time in the five months we'd been together. Never about Annie directly, but instead about stupid little things. So I wanted to take it easy for a while, to work on our relationship without adding any additional complications, but Cassandra had another idea.

After the night we'd spent with Annie, Cassandra had told me of a fantasy of hers. She wanted to be with two guys. Furthermore, she wanted the guys to have sex with each other. I'd agreed at the time, but in the disastrous aftermath of the Annie affair, I kind of hoped that Cassandra would drop the idea. No such luck. She talked about it a lot, always implying that I owed it to her since she had helped me fulfill my greatest fantasy.

For some reason, any indication that I gave that I might have sexual feelings for men turned Cassandra on like you wouldn't believe. She was wild about snowballs and cream pies; feeding my come back to me either from her mouth or her pussy. She also liked fucking me in the ass with her dildo. Cassandra was really into gay porn as well, and she loved hearing me tell her about what I'd do if I was ever with a man. Just talking about it got her so hot, she would fuck my brains out.

"Pretend I'm a boy," she would say sometimes, offering me her tight little ass.

This was all sort of fun, I'll admit. With Cassandra, I said I was bisexual because it turned her on so much. For a while I could actually make myself believe that I was. But when I thought about actually being with a man, outside of the realm of fantasy, I got a little freaked out and disgusted. Still, Cassandra wouldn't let it go.

There was a guy named Steve, who she said she knew from the town where she lived before she moved here. She said that he wasn't gay but, like me, was curious to have sex with a man at least once in his lifetime.

"You'll like him," she insisted. "He's really cool and pretty good looking."

I didn't want to commit to actually agreeing to have sex with this guy, and managed to skirt the issue for a long time. Then, one day Cassandra announced that Steve was coming to town for the weekend. He'd already reserved a hotel room, a suite with a hot tub. It was clear that Cassandra expected us to spend the weekend with him.

I balked at the idea, and this provoked the worst screaming argument Cassandra and I had ever had.

"You promised!" she kept saying.

I could not recall ever actually promising any such thing, but that didn't matter. In Cassandra's mind I had. Finally, as we veered towards the cliff's edge of break-up, I consented. Emotional extortion isn't exactly a turn-on for me, but I was terrified of losing Cassandra. And she was so happy and relieved when I finally agreed to the three-way that I was able to believe that it might be worth it after all. We had our first taste of make-up sex that night, and it was as hotter than it had been between us for weeks.

So, nervous as hell, that Friday night I met Cassandra's friend Steve. We went out to dinner together and, strangely, meeting him put me at ease. He was good-looking, but not too good-looking, if you know what I mean. If he was out-and-out ugly, I wouldn't have been into it at all, but if on the other hand he was some kind of GQ-looking jock type, I would have been so intimidated that I would have bailed right then even if it meant losing Cassandra forever. But Steve was a regular-looking guy. About my height (5'7",) with dark hair and blue eyes, the same as me. He had a neatly-trimmed goatee, and a congenial smile. He was perhaps in a little better shape than me, muscular in a wiry sort of way. He also had a dusky, weathered look to him, which made him look much older, though I knew he was only a couple years older than Cassandra and I (we were nineteen at the time.)

His personality was as easy-going as his looks, and for this I was even more grateful. He had good sense of humor without coming off as obnoxious or over-bearing. He was easy to talk to, especially after the second bottle of wine was brought to our table. (Thank God the waiter didn't card us. This episode would have been unthinkable without the lubricating factor of alcohol.) The conversation was neutral; we talked movies, we talked music, we talked about the war (this was 1990, during the first Gulf War.) Steve had been in the Army, but seemed happy that he had got out before he actually had to shoot anybody. The topic of what we were planning to do to one another that night was completely unspoken, but I know it was at the front of all of our minds.

Cassandra was very attentive to me throughout the dinner. She gave no outward sign that she was hot for this other guy, and that helped me out a lot. On top of my anxiety about homosexual experimentation, I was also dealing with this creeping feeling of jealousy about seeing Cassandra with another man. But Cassandra diffused this as best she could. She sat close to me, was openly affectionate, and even groped me under the table a little.

I should also mention that she looked unbelievably hot. She wore this tiny black fuck-me dress and I knew she didn't have anything on underneath. (Cassandra was never big on panties, and I don't think she even owned a bra.) Her breasts were about half exposed, and her nipples stood out against the thin fabric like fat pieces of candy. Steve, try as he might, couldn't keep his eyes off of her, but this didn't bother me as much as I thought it might have. Cassandra was with me, not with him, and this gave me real pride. Enough so that the thought of sharing her with him began to lose its edge of anxiety and become something I was almost looking forward to.

Talking to Steve, I would force myself to think about what was really going on. I visualized sucking his cock, and this mental picture gave me such a hot twinge that for a time I was unable to speak anything more than yes or no responses.

At one point, he got up to go to the bathroom, and Cassandra caught me checking out his ass as he was walking away. I wasn't even really aware that I was doing it until she said: "Cute, isn't it?"

I looked away guiltily.

"What do you think?" she asked.

"I think we're going to need another bottle of wine," I said, deflecting as best I could.

"But are you into this?"

Instead of answering, I guided her hand to my lap so she could feel for herself. When she found how hard I was, she squealed with delight and gave a deep soul kiss which only raised my temperature more. We were still going at it when Steve came back.

"Hey, where's my kiss?" He was looking right at me when he said it.

We left the restaurant shortly after that. The third bottle of wine was procured at a liquor store on the way to Steve's hotel. When we got to the room, he broke out a bag of weed which could only grease the skids further. We poured out the wine into paper cups, and Steve rolled us a fattie.

Even with the intoxicants, there was a heavy awkwardness in the air. Nobody was sure how to get this started. Back at the restaurant, we could pretend that we were just on a social outing, but here in the hotel room it was obvious what we had come to do. The conversation just died and we smoked that whole joint without saying a word. We were sitting together on a couch, close, with me in the middle. Steve was pressed against me closer than I'd ever been to another man. This was a little unsettling, and I tended to lean the other way, into Cassandra.

On one of the passes, instead of handing me the joint, Steve held it to my lips. This was an intimate gesture, and I actually kissed his fingers lightly. Even this tiny male-to-male contact made my stomach tremble. He looked over at me with such intensity that I had to look away.

Cassandra stretched herself out across both our laps then. Steve took a deep drag from the joint, and leaned over to blow the smoke into Cassandra's mouth. They kissed, sweet-smelling smoke curling from their mouths, and I felt a slight flush of outrage. This guy was kissing my girl. Then I recalled how I had started the night with Annie by kissing her in front of Cassandra. I wondered if this was payback.

I pulled down a strap on Cassandra's dress, exposing one of her luscious little tits. I toyed with her fat steely nipple and Cassandra moaned, writhing into my touch. Steve sat up so he could watch. He reached down and freed her other breast; began to stroke it. Cassandra squirmed on our swollen laps. I turned to look at Steve and he surprised me by kissing me full on the mouth.

In the fantasies I had shared with Cassandra, I had imagined sucking cock and even getting fucked in the ass, but for some reason I had never considered kissing a man. It was so shocking that at first I pulled away, but then I relaxed and let his lips open mine. The tickle of his facial hair was strange and appalling, but was exciting because of its very wrongness. I surrendered to it, allowed his tongue to penetrate his mouth, tasted the wine and the smoke on his breath. After what felt like a very long time, I actually kissed him back.

When we finally pulled apart, Cassandra was looking up at us with rapt fascination. Her hand had wandered down between her legs and she was stroking herself as she watched us kiss.

"Let's get in the hot tub," she gasped.

We undressed then. Cassandra fastest because all she had to do was to pull her dress off over her head, Steve and I more slowly because we couldn't take our eyes off each other. It was another awkward moment, and I wondered if gay man had to contend with this every time they went to bed with someone new. I'm talking about the anxiety of wondering how your cock is going to measure up to the other fellow's.

Steve slid off his jeans and his boxer shorts and I was relieved to see that he was about the same size as me. Between half and three-quarters erect (call it five-eighths, if you want.) I've never been one for ruler-based descriptions, but for the sake of clarity let's say that he was about six inches with the potential to go to seven at full mast. And thick, Jesus. I think I actually licked my lips when I saw it.

I pulled my pants off and I Steve's eyes went to my cock with the same concentration that I had bestowed upon his. We three slid into the churning water, Cassandra in the middle this time. While I was still trying to acclimate myself to the searing heat, Cassandra sidled over to Steve and the two of them began to make out fervently. I wondered what their history was, if they had ever fucked before. They certainly seemed familiar with one another. Again I felt the flush of jealousy but, weirdly, this turned me on even more.

I grabbed Cassandra from behind and she pressed her ass back against my quivering erection. I reached around between them and toyed with Cassie's tits as she and Steve desperately kissed. Then, growing bold, my hand dove under the water. There was a second of uncertainty as I decided whose sex I wanted to touch. I made up my mind and for the first time in my life another man's cock filled my hand.

I squeezed him under the water and felt him swell up in my palm. It was weird. I had of course jerked off about ten thousand times in my life, so holding a cock in my hand was not a new sensation. But another man's cock, that was an entirely different proposition. It felt strange and new. Experimentally, I stroked. Steve groaned and the three of us pressed even closer together. My own cock slid between Cassandra's buttocks and she wiggled against me. My head pressed against her asshole, with not quite enough pressure to penetrate. With my hand, I guided Steve's prick into Cassandra's eager pussy. She gasped and arched her back against me as the other man fucked her under the water, leaning over to lap the water from her tits.

I put my arms around Steve's back, pinning Cassandra between us. I wanted to fuck her ass while Steve was in her pussy, but I couldn't get the leverage. Instead, I just rubbed myself against her, leaning forward over her shoulder to kiss the man who was fucking her.

We held her so tightly between us that when she came we both felt it as a sudden gasping tension, followed by a shuddering release.

Steve pulled out of her and climbed out of the water, sitting on the edge of the tub. He looked down at his rail-spike hard-on and then he looked at me. I knew what he wanted and, surprising myself, I wanted it too. I slid between his legs and lowered my head onto his lap. I took his cock into my mouth.

He was so fat and ripe in my mouth, tasting slightly of Cassie's pussy juices, but with a muskier, saltier flavor that was all his own. The cock twitched into my mouth as I went to work on him. I tried to blow him as Cassandra blew me, focusing most of my attention on his fat, bulbous head. The urge to do the head-bob thing was for some reason great. It just felt natural to mouth-fuck him, so I did that for a while, his prick getting juicier and juicier as I worked.

Cassandra had slid behind me and reached her hand down to stroke me while I sucked her friend. I felt her light, fluttery kisses all up and down the back of my neck.

Cassandra, who had to be about the best cocksucker in the world, sometimes talked as she went down on me, moaning and slurping and saying things like "oh God I love your sweet prick." I didn't talk, I would have been embarrassed to say anything like that, but in that moment I knew how she felt. I loved Steve's sweet prick. I really did. I was crazy for it, hungry and wild. I let him slide out of my mouth and licked him all up and down the length of the shaft like he was an ice cream cone. I lapped at his balls and jerked his prick, which was slick with my own saliva. Then I took him into my mouth again and sucked him hard and tight.

Steve tried to pull back. "I don't want to come yet," he said. But I wanted him to. I wanted it badly. I wanted to see if he tasted like me. But I let him go. I looked up at him and smiled.

"You little faggot," he said, affectionately. "You can not tell me you've never done that before."

"You're the first," I said. Steve leaned down and kissed me again. I wanted him to now. He was a good kisser.

"Let's go to bed," Cassandra whispered into my ear. Strangely, for a few seconds I had forgotten that she was even there.

Not even bothering to towel off, the three of us ran dripping to the bed, soaking the sheets, laughing and rolling around together.

I fell between Cassie's legs and lapped at her dripping wet pussy, just for the contrast of sucking a woman so soon after sucking a man. She giggled and wrapped her legs around my neck as I buried my face in her twitching snatch. Then her laughter became suddenly muffled and I realized that her mouth had been filled with Steve's cock.

I twisted on the bed, working myself around so Steve could suck me if he wanted to. I felt his mouth wrap tentatively around my prick. His mouth was stronger than Cassie's was, lips and tongue and sucking breath all exerting more pressure down there than I was used to. He wasn't as skillful as Cassandra was, either. It was almost too rough. Not exactly unpleasant, but I found myself drawing away from him a little anyway. Our three-way 69 (should that be called a 696 or a 969?) only lasted for a few minutes.

Cassandra got on her hands and knees and twisted around. She took me in her mouth and proceeded to renew her claim upon my cock. She was fantastic. Steve got behind her and fucked her from the back. Cassandra moved in and out between us, her mouth and pussy simultaneously filled. I knew this was a fantasy of hers, she'd told me before that she wanted to suck a man while another fucked her. I could tell by the way she purred as she blew me that she was coming.

Steve pulled out of her and lay back on the bed. "God, I'm so close," he said. His cock twitched as if he was about to shoot off into the air. I crawled over to him.

"Come in my mouth," I said. It sounded like I was begging for it.

Steve nodded and I took him into my mouth again. It didn't take much effort on my part to make him squirt. Any apprehension I might have had evaporated as soon as I tasted it. When Cassandra fed my come back to me, it was thick and salty, with this underlying slimy bitterness. Definitely an acquired taste. But Steve's stuff was thinner and more watery. The taste was meatier, I don't know how else to describe it. I thought of caviar. I thought of raw oysters. I gulped and swallowed eagerly, relishing the feeling that I had become a cocksucking come-slut. A gayboy. Almost a woman.

It was like baptism.

I licked him clean and looked up to find that Cassandra was regarding me with straightforward awe.

"Jesus, that was cool," she said, laying back on the pillows and spreading her legs wide. "Oh, fuck me, Christian. Fuck me hard."

I climbed on top of her and drove it home. After less than a minute of desperate, brutal fucking, I pumped Cassandra full and felt her cunt spasm around my cock so tight it was almost painful.

I pulled out, exhausted, and looked down at the sloppy white mess I had made of her pussy. Steve looked at it too. Before Cassandra could even catch her breath, he dived in there and began to slurp my seed from her glistening chalice. She bucked her hips to meet his dripping chin and I could tell she was getting off yet again. Steve made these very gratifying yummy noises like he was drinking a sweet creamy milkshake.

Then something kind of strange happened.

"God, yes," Cassandra cried out. "Oh, God Carson."


Carson was Cassandra's brother's name. She had confessed to me once that she'd had an incestuous affair with him. (See "Cassandra's Secret.") What the fuck? Had Cassandra, in the extremity of her passion, accidentally called Steve by her brother's name? I kind of doubted it, but the alternative was almost too much for my mind to bear.

The aftershocks of her umpteenth orgasm fading away, Cassandra lay back utterly satisfied. She gave no sign that she was aware of the fatal slip she had made. If Steve (if that was his name) realized it, he likewise gave no sign. The three of us curled up together, dripping wet and done in. Within a few minutes, they were both snoring, but I laid there awake, my brain going wild.

Had Cassandra lied to me? Had I just participated in whatever sick fucking game she played with her brother? She'd told me how crazily obsessive the whole affair had left her, but she'd insisted that she loved me now, and had left Carson behind. Was that a lie, too?

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byChristian Black© 2 comments/ 85966 views/ 8 favorites

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