A gay story: The Education of Lisa Ch. 09 The next night, as Will and I were going to bed, I reminded him that he had promised me another story. Will was slipping into a black teddy, with a ridiculous amount of red, furry fringe. (I’d worn the silly thing only once, at Will’s insistence that he wasn’t turned on by anything that hasn’t been pre-worn by me.) By now, though, I was getting used to seeing my boyfriend in my underwear. I was even able to sort of ignore the fact.
The night before, he had finally told me the story of how he’d lost his virginity. He did lawn work for a neighbor, had the hots for the young daughter, but ended up sleeping with her mother. I also found out that the mother was none other than his ex-wife Carol. When I asked him if he’d slept with any women besides me and his ex-wife, Will gave a somewhat troubling answer:
“Women? No.”
I finally dragged out of him that he’d had sex with a man. I was a little too overwhelmed then to hear the details, and Will had promised to tell me tonight. I couldn’t think about anything else all day. For some weird reason, the thought of Will with another man made me more jealous than thinking of him with a woman. At the same time, though, it definitely turned me on.
“Do you remember the story you promised to tell me tonight?”
“Yes,” Will said, blushing slightly.
“Do you still want to tell me?
“Do you still want to hear it?”
“Yes,” I said. I was tingly with anticipation.
“Well, OK, like I said I was in my last year of college,” Will began. “Carol and I were seeing each other pretty seriously. We’d already announced our engagement and everything. So, when the fall semester ended, instead of going home to my parent’s house like I usually did, I went with Carol to visit her brother in San Francisco.”
“I hadn’t met any of her family yet. I think none of them approved of our marriage because of how young I was. I mean, I was twenty-three and she was, let’s see, forty-four.”
“Oh my God,” I said, doing the math for the first time.
“She seemed a lot younger than that,” Will shrugged. “Anyway, her brother was kind of on the outs with the family, too, because he was gay.”
“So, he’s the guy you had sex with? Carol’s brother?”
Will smiled in a funny kind of way. I could tell that he’d meant that detail to be the big twist in his story, and I’d just spoiled it for him.
“You guessed it,” he said with disappointment.
“Tell me how it happened,” I pressed.
“OK,” Will sighed. “So we flew out to California and went to her brother’s house. He had this great little townhouse, must have cost him a fortune. There was even a guest bedroom where Carol and I could sleep, except . . .” Will’s voice trailed off for a few minutes. “Except she never slept there.”
“Why not?”
“She used to live in San Francisco,” Will said. “There was a guy there named Dennis who she used to see. I think he was the whole reason we went there in the first place. She’d got in touch with Dennis over the internet, and they rekindled their flame or whatever.”
“And she flew you out there while she fucked him?” I was aghast. “That’s terrible.”
“That’s Carol,” Will said. “It wasn’t the first time she’d cheated on me. She was really into going out to bars and meeting guys for one-night stands. She said that sex with me was boring, and that she needed to spice things up a bit. Of course, she promised me she’d stop when we got married, but . . .”
“The more I hear about this bitch, the more I hate her,” I said.
“Well, hindsight’s twenty-twenty,” he said. “At the time, it somehow didn’t seem that weird. We were even happy together, in a way.”
“That’s messed up, Will,” I said. “Anyway, the brother . . .”
“Yeah,” Will smiled a little bit. The memory was obviously a fond one. “His name was Harold. He was a video director, commercials and industrial training films, that sort of thing. He was younger than Carol, but still older than me, obviously, maybe in his mid-thirties.”
“Was he good-looking?” I asked.
“I don’t know,” Will said. “I guess so. It’s hard for me to say, because I don’t really look at guys like that. Harold had sort of a darker complexion than Carol, real dark eyebrows and this little beard thing. He shaved his head, though. I guess he worked out, because he was in pretty good shape. Dressed well, too.”
“He was a nice guy. Easy to talk to. Actually stood up for me a few times when Carol started ragging on me. Harold didn’t say anything about Carol sleeping at this other guy’s house, but it was obvious he knew.”
“So, this was the second or third night we were out there. I got out of bed because I had to pee. On my way to the bathroom, I saw that Harold was home from work and was sitting on the couch, watching TV and drinking a beer.”
“When I came out of the bathroom, and I could hear that he was watching ‘American Beauty’ on cable. I’d never seen that movie before, so I sort of watched it for a while from the doorway until he saw me there.”
“‘Can’t sleep?’ he said.”
“I said no, and then he told me I could come sit down if I wanted to and watch the movie with him. It had just started, and I had a hard time sleeping when Carol was out anyway, and I guess I was feeling kind of lonely, so I sat down beside him on the couch and we watched the movie for a while without saying anything.”
“Then he got up to get another beer. He asked me if I wanted one, and I said yes, even though I didn’t drink much. A beer sounded good, though. So gives me a Heinekin and we start talking, only sort of watching the movie.”
“He asks me about Carol, you know like polite questions about our relationship, then out of the blue he asks: ‘Doesn’t it bother you that she’s out screwing this other guy?'”
“‘Not really,’ I said.”
“‘Sorry, Will, but I kind of think that’s bullshit. My room’s right next to yours. I hear you crying yourself to sleep every night.'”
“You cried yourself to sleep?” I asked. I hated Will’s ex more and more with everything like this he told me.
“I tried to be quiet,” Will said, a little defensively. “I didn’t know what to say to him about that, so I just went out to the kitchen and got two more beers. When I got back, he said: ‘OK, I’m just going to say one thing then I’ll butt out. Carol’s my sister and I guess I love her in a way, but she can be just about the coldest, meanest bitch on the planet when she wants to be. I know you’ve seen it. She treats you really badly. She’s always putting you down. And now she’s blatantly fucking around on you. You’re a good-looking guy, and a real sweetheart. You deserve better.'”
“He was right, you know,” I said.
“Yeah,” Will said, “but at the time my first inclination was to defend Carol, deny that it bothered me how she acted, etcetera. But I was too uncomfortable to even do that, so I just started watching the movie again. You’ve seen it, right?”
“‘American Beauty?'” I said. “Yeah.”
“Remember the part when the weird neighbor kid, the pot dealer who was always shooting videos, when he showed the girl the video with the plastic bag blowing around in the wind?”
“I think so,” I said.
“It’s a weirdly intense moment in the movie. I think it’s when the girl kisses him for the first time. Anyway, right when this scene is playing, I feel Harold’s hand on my shoulder. It was scary at first, but then again I kind of wanted him to touch me.”
“‘You are so tense,’ he said.”
“Then he told me that he’d been a massage therapist when he was in school, and that he wanted to give me a massage.”
“Did you realize by then that he was coming on to you?” I asked. With anybody else, it would have been obvious, but Will was kind of dense about things like that.
“I don’t know,” Will said. “I guess part of me kind of did, but mostly I was just grateful for the company, and for the fact that he was so nice to me. It made for a welcome contrast to Carol.”
“So he goes off into his bedroom and he comes back with a blanket which he spreads out on the floor. He tells me to take off my shirt and lay down. Then he rubbed some kind of oil on his hands. I don’t know what it was, but it smelled really nice. He started massaging me. My neck, my shoulders, my back. It felt incredible. He had really strong hands, but his touch was so light and warm. I just melted. I’d only had two beers, but my alcohol tolerance was next to nothing, so I was buzzed from that on top of everything else. I felt warm and relaxed all over. Except . . .”
Will grinned.
“Except what?” I asked.
“Except I started to get a hard-on. A really strong one, you know? I couldn’t help it. What he was doing felt so good. Plus, there was some gay stuff in the movie and so that was on my mind. So I had all these mixed emotions. I was turned on, and at the same time a little weirded out because I was turned on. By a guy. I never wanted the massage to end, because I was scared of what was going to happen. But at the same time, I knew that I would go along with anything he wanted to do. Anything.”
“His hands kept working lower and lower, until he was at the waistband of the sweatpants I was wearing. Then he worked inside, and started rubbing the tops of my buttocks, and that was it. I couldn’t take anymore. I rolled over and looked up at him. He looked back down at me, then he leaned over and kissed me.”
“I’d never even imagined kissing a man before. It was different. His mouth was rougher than Carol’s, stronger. I could taste beer and cigarettes on his breath, but at the time I really liked it. His hand reached down and touched me through my pants. I kind of writhed into his touch because I wanted him to feel how hard I was, how hard he’d made me.”
“He said: ‘I know you’re not gay, Will, but I’d really like to suck your cock. You don’t have to do anything to me if you don’t want to, but I’d like to do that one thing for you. Trust me, a blow job will work wonders for your self-esteem.'”
“I was too breathless to even say yes, but I didn’t have too. He pulled at my pants and I lifted up my hips so he could slide them off. I was laying there naked.”
“For a few minutes, he just touched and kissed me all over, rubbing my chest, sucking my nipples, working his way down so slowly I thought I was going to lose my mind. Then he got between my legs and he went to work.”
“His mouth and his hands were all over me down there. My dick, my balls, even down between my legs and around my asshole. Slow, wet licking, touching, kissing. Sucking. It was Heaven. Carol had given me blowjobs a few times, back when we were first going out, but it had been a long time and it had never been like this. Like he was worshipping me down there. Like he loved my body.”
“Jesus, Will,” I gasped. I was getting very aroused and cursed the fact that I was on my period. There was not much I could do about my arousal that wouldn’t make a terrible mess.
“He stopped a few times, and said things like: ‘I love your beautiful cock,’ and ‘You taste so good, so musky and manly,’ and ‘Don’t be afraid to come. I want you to. I want to eat it.’ Then he was just sucking me. He started with kissing and licking the head, but gradually worked me in deeper until I was in his throat. His hands were busy the whole time. The tips of two fingers, slicked up, worked around the rim of my asshole and slid inside a little. With his other hand, he fed my cock into his throat. He started making these little gulping motions, sucking me in deeper and deeper. It was incredible. Then he plunged his fingers into my ass as far as they would go and it was like pushing a button. I shot off down his throat. The tip of my cock burned, it was so intense and alive. He swallowed every drop. Just sucked me dry.”
“Oh my God,” I said. I licked my own fingers and started rubbing my clit. I couldn’t help it.
“So Harold sat up. He said, ‘I’m going to jack off now. I’d like you to watch.’ He slid out of his pants and pulled out his dick. He was huge. I was surprised. I’d seen other guy’s dicks, you know in the locker room at school or whatever, but I’d never seen one so big. He was way bigger than me.”
“He started stroking it and I could tell that he was showing off a little. He knew how big he was, knew that I was impressed. It was so cool, watching him work that huge thing. As soon as I caught my breath, I crawled over to him and said: ‘How about this instead?’ Then I took him in my mouth.”
“You sucked his cock?” I said, rubbing myself furiously by now, my fingers no doubt tinted pink.
“Yeah,” Will said. “I wasn’t sure I was doing it right, I was so nervous. I had this huge fleshy prick filling my mouth. It tasted all, I don’t know, musky I guess. Like he said. I hadn’t expected the taste to be so strong. I tried to suck it all in, like he’d done to me, but it was too much. I gagged a little and started to panic. Then he pulled my head away, gently, and he said: ‘Throat action takes a little practice, Will. This is your first time, just pretend it’s an ice cream cone. I don’t even have to come in your mouth if you’re not ready for that.'”
“I said: ‘I want you to. You tasted mine. I want to taste yours.'”
“He smiled at me and said: ‘OK, but I’ll let you know when I’m about to, so you’ll be ready for it.'”
“I went back to work on him, just licking and sucking the head mainly. I still didn’t know if I was doing it right, I was so inexperienced, but Harold started moving with me and making these little moaning noises. I thought maybe he was just doing it to be polite, but whatever. I was so into it. So into his cock. I wanted him to come so badly. I wanted to taste it.”
“I think he was about to, because his cock was really twitching and moving and I think even getting harder. The taste was changing, too, getting wetter and saltier. I think a few drops might have come out. Then the door burst open and I hear this voice say: ‘Oh my fucking God!'”
“Carol came home?” I stopped stroking myself and looked at Will with disbelief.
“Yeah,” Will said. “I guess she had a fight with her other guy. So she bursts in the door and catches me with her brother’s cock in my mouth.”
“Oh my God, Will, what did she do?”
“Freaked out,” Will said. “Screaming. Saying stuff like, ‘I knew my brother was a faggot, Will, but I never knew you were a cocksucker.'”
“Then Harold started screaming back at her, and they went at each other. I thought for sure the neighbors would call the cops. I just wanted to disappear, you know? Just shrink away until I was invisible. I did not want to be between those two.”
“Carol told me that she wanted to break up with me, couldn’t stand living with a cocksucking faggot of a boyfriend, etcetera, etcetera. Then, and this is the shameful part, I started crying. Started begging for her forgiveness. Harold started yelling at me, then. Told me to grow a pair of balls. It was a horrible scene.”
“Then Carol calmed down a little, and she got this weird look in her eyes and she said: ‘Fine. You want to fuck my brother, that’s fine. Fuck him right now. I want to see it.’ She was serious. She wanted to watch.”
“With her brother?” I said. “That’s really messed up.”
“Yeah, well, Carol was all about control. That was her fetish. Me getting with Harold behind her back, that was something she couldn’t control. Her making us have sex while she watched, that was her way of getting control back. Harold told me later that she’d watched him have sex with one of his boyfriends from high school. He said she threatened to tell their parents that he was gay if he wouldn’t let her watch.”
“Harold was dead against it at first, but she started working on him hard. He was, for all his talk, as much under her thumb as I was. Finally he caved in. He said that he had to be high first, though. He had a little bit of hashish and we all smoked some.”
“You smoked hash?” I said. I had never suspected Will of doing any kind of drug.
“Yeah,” he said. “It gave the whole scene this weird, dream-like quality. Carol told Harold to put on some porn, and so he played a video. Guys dressed up like it was an ancient Roman orgy, fucking and sucking. I watched it for a while, stoned out of my mind. Then Carol told Harold to get on his hands and knees before me. He gave me a condom, but Carol said: ‘Trust me, Will doesn’t need to wear a rubber. He’s never fucked anybody but me.’ So Harold just took some of the massage oil and worked it into his asshole and nodded at me when he was ready.”
“So I got on the floor behind him, and slid inside.”
“Oh,” I moaned. I was stroking myself again, the picture in my head so clear. Will, my man, fucking another man in the ass.
“He was so tight,” Will said. “It felt so different than Carol’s vagina. More familiar, I guess. More homey.”
“Homey?” I laughed despite myself.
“I don’t know how to describe it,” Will said. “It was more inviting, somehow. More welcoming. He started to move with me, pushing back against me when I drove it inside him, then pulling away when I pulled out. So deep and perfect and complete. It was like something alive between us. Something I’d never felt with Carol. Something I never felt again until I got with you, Lisa.”
“I think Carol wanted to ruin what I had with Harold, by controlling it, by watching it. But this thing between us was almost like music. Like music made by my cock in his ass. I don’t know how else to describe it, but it was something she couldn’t touch, something entirely beyond her reach. She was across the room, masturbating, watching, and I could sense that she knew things were getting out of hand. Because she quit playing with herself and said, ‘All right, that’s enough. Stop.'”
“Only I didn’t stop. I was so close to the edge. Harold was moving inside his body, squeezing me, embracing my cock with his muscles, like a kind and loving caress. I came inside him, and this too was like a secret we shared. Something Carol couldn’t see, something she had no command over.”
“I pulled out and sat back on the couch, trying to catch my breath. Harold sat beside me and started stroking his cock again. I realized that I had come twice, but he hadn’t come at all. I wanted to suck him, but before I even had the chance, he was spurting off all over the place. All over his belly and chest, huge splats of semen. When he was done, I leaned over and started licking it off him. It was wonderful, ambrosial.”
The image of Will licking semen off another man’s belly was enough to send me over the edge. I came so hard I cried out.
“Carol actually came over and pulled me away from him. She said: ‘I told you that was enough, you little cum-guzzling freak.’ Then she started screaming again. I don’t think she’d expected us to like it so much.”
“We went home the next day. Harold and I wrote back and forth for a while. He wanted me to leave her, to come live with him, but I felt guilty about what we did. Not just because of the gay thing, more like I was being disloyal to Carol. Finally, he gave me an ultimatum. I had to choose, him or her. I chose her. He never spoke to me again. Didn’t even come to the wedding.”
Will sighed heavily. He had come to the end of the story, and I don’t think he’d anticipated the sadness.
“Did you ever think about being with another guy?” I asked.
“I thought about it, sure,” Will said. “But I never had another opportunity. Plus, Carol never let me live it down. Every time she was mad at me, she’d call me faggot, cocksucker, whatever. So I tried to deny how much I’d liked it, even to myself. And now I’m with you, and I don’t plan on cheating.”
“I wouldn’t mind,” I said, without thinking. “If it was with another man. It wouldn’t bother me like a woman would. It’d be different.” As soon as I said that, I wondered if it was really true.
“That’s nice of you to say, Lisa,” Will said. “Still, it’s not going to happen anytime soon. Now, was that enough of a bedtime story?”
“Yes,” I said, kissing him good-night. “Thank you.”
He turned out the light. I laid beside him for several minutes before I said: “Will?”
“Yes?”
“I want you to fuck me in the ass.”
“What?” he said. “I thought you didn’t like that.”
My first boyfriend Jerry had been a serious anal obsessive, and I’d always sworn that I’d had enough sodomy with him to last two lifetimes. But now, after that story, I felt like I had to reclaim Will again. I wanted to show him that I could give him everything Harold could. I obviously didn’t have a penis, but I did have an asshole, and if I gave it to Will, it would be taking back the little part of him that I felt like I’d lost to the memory of his experience with a man. Or at least, that was my thought process.
I turned my back to him, and Will squirted something cool and slick into my anus. He slid inside with the same care and gentleness with which he did everything else. I realized as I took him into my most secret place that this was the last barrier, the one place I’d never taken him. I moved with him as I imagined Harold had, trying to make music like Will said. I embraced him inside. Loved his cock with my ass. Wished in that moment that I was a man, that I had a cock instead of a bleeding vagina. Wished that Will would lap the pearly beads of semen off my lightly fuzzed belly. I came when he came, in a dark and secret way.