I Couldn't Figure Him
From Gaynity Wiki
Author: Anon
++If you are a gay, or bi adult only and over 18 of course you are welcome.
[edit] 1
I met Orlando, "Call me Lando," he instructed right off, at my dad's golf club. We were the same age, about 22, probably the only younger men there. The rest were rich pot-bellied guys; some who ogled me in the showers.
"You the Gold kid?" he asked somewhat aggressively.
"Yeah, Jesse, you got a message for me?"
He laughed. "You don't play golf. I see you almost every Sunday, reading under these trees. Why do you come to a golf club if you don't play."
"Golf is for old fucks. Do you play?"
"Naw, I just use the tennis court, but if is hard to find someone to play with. Tennis?"
"No."
"What are your interests, as the teacher asks?"
"Sex I guess."
Lando stared at me. This was moving awful quickly into an intimate encounter. "You gay?"
"No, fucking no."
"Okay, don't get your balls in an uproar. If you were, I wouldn't blow your cover. Hey, that's kinda a joke."
We fell quiet. What did Lando see when he decided to approach me: a very tall, 6' 4" skinny guy with heavy black hair falling over my forehead, pleasant, even features, no movie star.
I appraised him: About 5' 7", brown hair with naturally tanned skin likely from a Mediterranean ancestor. He was wearing a light blue athletic shirt. It showed off his heavy upper arm muscles and his puffed out pecs. This was a muscle boy, no doubt.
He cleared his throat, "Lotsa rich young bitch girls here. My female parent is after me to amalgamate."
"Yeah," I laughed. "I get that all the time. My dad says it's just as easy to marry a rich girl."
"Is your dad rich?"
"He says we are the poorest ones here."
"How about you?" I asked, figuring we had reached a stage that it was okay to pry.
"We're filthy rich. Dad has a big stock position in IBM, got it back years ago."
Lando tried again, "So, you must be interested in something. Got hobbies?"
"I write."
"Yeah, what kinda writing."
"Short stories and now working on a novel." I patted my notebook.
"Can I read it?"
"Wait until it's published."
"When will that be?"
"Probably never."
"You know, Lando, I see you around. You dress really well, good jackets and pants and all, my clothes just seem to look ridiculous on me. What's the secret."?
"Good fit. If it fits, it will look good regardless. No matter which side you dress on."
"Huh?"
Don't they ask you that when you get your pants made? I've seen you in the showers, you're huge."
Shit, guys don't usually talk about other guy's equipment, at least not straight guys. Maybe this tough looking kid is trying to hit on me. I am horny and bored. Let's go with the flow. (This all passed through my mind.)
We discovered later in the conversation that we were both recently out of service. This was 1945. We both were in the air force, he stationed in the US, me overseas for three years in the pacific..
"So I heard about tennis, what else?"
He took off his shirt at this moment. As I got to know Lando, he would shed his shirt at a moments notice. His hand wandered over his nipples, pink surrounded by his smooth tan skin. Was he being provocative."? "I box."
"Huh?"
"I was champ at my air base."
"Wow." Now I was readjusting this gay/straight thing in my mind. Of course, there are rough guys who like to be serviced. But as I got to know him, he had a least three girls he was fucking.
"So you are a dangerous dude. Any soft spots?"
"I play the violin. In fact I am concretizing here at the club tonight."
I stayed after dinner to hear his concert in the conservatory room. It was something to see him play. His face was mobile, affected by the mood of his renditions. I'm no expert, but to me his selections and his style seemed absolutely genius.
We continued to see each other on Saturdays. One Saturday he asked if he could have the key to my apartment. He wanted to bring his current girl, Nicky up for some serious fucking. I wasn't too crazy about giving my key, but he fixed me with his eyes so pleadingly and perhaps commandingly that I handed them over with the proviso that he would be out by ten o'clock.
I met a girl at a resort. She lived in Boston. The first night we met I was able to get her in the back of my car in the parking area and in this cramped space was able to quickly seduce her. She was not a beauty, but she was easy, and I loved the way she got off so enthusiastically. It made me feel like the great lover I'm not.
I used to drive from Long Island up to Boston. Incredible how far my prick would take me for an easy fuck. I told Lando about her. "Let's double fuck-date, me and Nicky, you and....what's her name, oh Vikki. Hey Vikki and Nicky, what are the other seven dwarf names?"
It is true, both girls were about five feet tall and very cute. The evening came. It was a Friday. Vikki was having the fantasy that we were married husband and wifey and she was cooking dinner. It made me nervous, but I knew she was happy and would fuck good later. Lando arrived with his girl. He had a bottle of Wild Turkey. As I got to know him, I realized that he was a heavy drinker, right from the bottle. Anyway he offered drinks, no one was interested. He had some heavy slugs then, of course removed his shirt. Nicky immediately got drooly over his chest and kept rubbing his nipples. I could see that his pants were poofing out and before long, he waved ta-ta at me and disappeared into the bedroom.
Vikki and I started kissing and making out on the living room couch. Pretty soon we were both naked and we had a Boston Tea Party. I know she wanted me to go down on her, but somehow her cooch didn't appeal. I was just catching my breath after putting my condom in a tissue and lighting a cigarette when Lando appeared wearing only his tighty-whiteys. This was the first time I saw his legs. They were excellent, real fighter's legs, thick and muscular. His pouch showed that he was still semi hard. "We did it, Nicky wants more, in fact, she wants you Jesse."
"What are you talking about?" I quickly covered up the naked Vikki.
"I mean, let's switch. You take my girl and I'll take yours." He wiggled his thick eyebrows at me."
I was intrigued, in fact I started to get hard again. I looked at Vikki questioningly. She whispered "No," fiercely so I guess it was no.
"Okay you babies, you're missing some fun. I guess I'll go back and boff her again."
When he left I asked Vikki if she wanted another round. She demurred.
Vikki and I got dressed and sat in the living room. We could hear their cries of lovemaking and somehow I thought Lando, at least, was putting on a show. I could clearly hear Lando commands to Nicky, "Yeah suck it good, take it deep."
Poor Vikki was embarrassed, but I just smiled and winked at her. She got up and put the radio on loud.
Finally the two insatiable lovers came out of the room, she was wearing my bathrobe and Lando was back in his moist front underwear. "Hey fucking makes me fucking hungry, let's go out and have something."
We did go for hamburgers and I drove Lando home and dropped off Nicky, Vikki robe with us in the backseat.
About a week or so later I was back at my reading station at the club. I saw Lando walking by himself, looking very dejected. When he was close enough to hail him, I did. He came over. "What's up Kid Galahad, you look like shit," I said.
"I have a real problem. No use involving you. Somehow I'll work it out."
"Come on, we're friends, what's up?"
"Well you must never mention this to anyone. It could affect my career. My father would cut off my Princeton tuition."
"I promise."
"Nicky missed two periods."
Now this was 1946, abortions were illegal and very expensive, if you wanted I good doctor instead of an auto mechanic. Apparently Lando had found a name in his father's roll-a-dex. Cost: $500.
"There's no way I can raise that."
Don't forget I was working. I didn't have that much money laying around but somehow I could put it together. "Lando, I'll lend you the money. Just pay me back in small installments when you can."
He surprised me by breaking in tears, stifling and wiping his nose with the back of his hand. "You're a beautiful guy. Thanks, I love you for this."
I wondered if I was just trying to get a more superior grip on our friendship, but in any event a week later Lando was all smiles. "She got her period. I'm dropping the bitch, she's too fertile. Hey, let's celebrate the end of my big trouble.
We went down to the Village, Greenwich Village. There is a bar there called Minetto's Tavern. We socked up two schooners of ale, Lando sweetened it with Wild Turkey from his back pocket. Some guy passed by and made a remark, I think to the table behind us, Lando jumped up and grabbed the guy by the shirt, he was a big hulking fellow. They scuffled, then Lando's fist shot out, the guy lay totally out on the floor. Lando had this ugly scowl on his face, he was drooling in anger. I had never seen him like this. This was the other side of the gentle violinist, the fighter.
I suggested we call it a night. I was afraid the guy's friends would clean up the room with us. Back in my apartment Lando was in full command again, but of course he was pretty drunk and he was drinking more. He wiped off his shirt and a new development, he took off his shoes and socks. Nice feet, I thought, curvy with back hairs on some of the toes.
"Take off your shirt too Jes,
"Naw, I'm fine."
He spoke firmly, very firmly, "I said take off your shirt!"
"Okay, okay." I was afraid he'd get violent, drunk as he was.
We sat down, both smoking. "Lando, why do you take off your shirt when we're together?"
"Don't you like it? Do you think I'm trying to seduce you?"
"Well something like that. Maybe you still think I'm gay."
"Jes, that is already established. I can see how you mentally eat up my feet, my chest, even how you study my lips and eyes. Maybe you don't know it yourself, but you will. If I made a move on you right now, you would not be able to resist."
"Why are you doing this?" I said it plaintively.
He laughed and took another swig from the bottle, I noted that it was almost finished. "You l-o-o-o-v-e me, don't you? I knew it immediately when you were willing to scrounge up that money for the abortion. No friend does that, only a lover."
He passed his hands over his left pec, stimulating his nipple that erected immediately. "It's yours to lick. I'm offering you free range of my body except my poop hole. Enjoy yourself, knock yourself out."
I stared at him, my mouth hanging open at this complete change in him. "Come on," he urged. I could use a good blowjob now. I know you never did it, but I'm patient, I'll teach you how to make Lando happy." He bent over and pulled his underwear down. I had never seen his privates before. His pubic hair was wild, lots of it above his dark tan circumcised cock. The pubes extended almost from hip to hip. His belly was smooth. His dark maroon balls hung long under his sizeable prick.
He came close to me. With one hand he shook his rapidly rising cock, his other hand rested on the back of my now sweaty neck. "Oh, how you long to put your lips on this. Tell me you want it."
I tried to pull away, but his sexual magnetism held me. Finally I expelled the breath I was holding. "Yes," I said softly.
He exerted a strong pressure on my neck and I slowly sank down on my knees. "That's it writing boy, stick your tongue out and take a taste. It's prime meat."
The tip had a drop of pre cum. I licked it. It tasted sweet. As my tongue passed over his cock head he let out a long sigh. "Oh yesss, you're getting with the program and I don't have to get rough with you. You're a good friend, I know you want me to enjoy this. Get your tongue into action."
I held the now stiff shaft in my fingers and lipped the head and the spot behind the head. He was now breathing hoarsely and his smooth hips were slightly bucking. "Take it all baby. I'm pretty hot. I won't take long. You'll love my spooge, all the girls do."
I allowed big flat head to enter my mouth and kept sucking and salivating around the shaft as he pushed deeper. I put my hand against his lower belly to stop his advance. "Okay, if that's all you will take, it'll still be good. Suck now, no more stalling."
I began a vigorous licking and sucking of his cock. I didn't realize that he was slightly pushing it deeper. "You're almost there Jes, open your hot throat and really make me happy."
He slipped all the way and his wiry pubes that had a musty smell were against my nose. I could sucks, it filled me, but I could swallow. He was now moaning continuously and grunting like a stuck pig. In spite of my awe at my own compliance, I was pleased he was having such a thrill. Suddenly he seemed to lock his knees, his cock seemed to grow and get stiffer. "Oh you shit head, you did it. I'm going come like I never did before. Get ready. Uh, uh, UH."
I felt his cum shoot straight down my gullet into my stomach. I withdrew a little and now tasted it. It was cloyingly sweet with a slight bitter taste. He had both hands around my head to steady himself. His legs were shaking and wobbly. Finally he slipped out of my mouth and fell on a nearby chair. "Fuck Jes, you're really good at this. I think I have helped you find a new talent. Say, what do you think about getting fucked in your skinny ass? I bet I could make you howl with fun. Oh yes, I suppose now you want to get off. Don't expect anything from me, but if you want to wank, I'll watch you. Some guys like that."
I finally got myself in some sort of shape. "Orlando (using his full name) This was nuts. I just got drunk. Never again."
He guffawed. "They all say that. Hey I'm pretty wrecked. Can I sleep here?
I nodded. "Take the couch. I'm going to take a shower and go to sleep."
He left while I was still asleep. I saw him the following weekend at the club but I turned away when he started to approach. Finally later that day, he collared me in the locker room. "Jes, I know you are pissed at me. I apologize for manhandling you. I can only say that I was drunk. Will you forgive me? I know that you are straight and that I shouldn't have done that."
He looked at me, his head on the side like a little dog. He squinted his eyes cutely, pursed his lips and said "please" again. Finally I broke out laughing and said, "Okay, I accept. But no more of that shit."
"Right. Now the reason I want to talk to you is about Pam Greber. You know the foxy girl, she is the daughter of that stock brokerage firm. Anyway she said that she thinks that WE are the hottest guys she ever saw and she wants to set up......are you ready.....a threesome."
I know that girl. She's movie-star gorgeous. Just the idea of sex with her got me semi hard. "Yeah, I could do her gladly."
"We need to use your place. Let's make it tomorrow, Sunday about two o'clock. She lives near me. I'll pick her up and bring her over."
"Okay, done and done."
End of Part One.
[edit] 2
I wasn't sure, socially, how you entertain the members of a three-way. While I waited for them, I setup an espresso pot, three cups and brandy and snifters. It looked nice there on the coffee table, you know civilized. Just then the door stairs bell rang and I pressed the release button. I could hear them coming up the flight of stairs to my apartment door. I opened the door, a fixed smile on my face. To my surprise Lando grabbed me and hugged me and even kissed my European style on my cheek. I took Pams slim cool hand, We looked at each other. Hell she sure was a looker. These two-shaded gray eyes in a sloe shape. It was hard to look steadily at them without your breathing deepening. Impulsively she also kissed my check, She giggled, "I kissed the other side, the girl's side it will always be known as.
Lando flopped on the couch and had already removed his blue oxford shirt. He also uncorked the brandy and poured himself a healthy portion. Then seeing us looking at him, he tilted the bottle toward each of us and when we nodded, he poured two other glasses.
I heard the espresso in the little kitchen making that "swosh" sound and I retrieved the pot and poured three small cups. We all spent a serious time drinking our brandy and cioffee,each wondering what was the next step. But Pam and I had no worries with impulsive Lando here. "May I take your blouse?" he asked gallantly. She stood and unbuttoned it. She was wearing no bra, but rather an athletic top. Pam was an excellent athlete, woman's champ at the club and had also won several tennis trophies. Her lean, strong body looked as if it was made for mountain climbing. I noticed that she had only small bumps in her breast area. None of my girl friends had small breasts and I found that slightly exciting, almost as if they were boy/girls.
Pam and Lando looked at me and said in unison, "Well?" I wasted no time, I put my hands at my waist and whipped my tee shirt off.
"Oh nice," Pam said. You are my male equivalent, skinny and strong. Lando is the bulging muscle type and I have a place in my heart for those boys too."
Suddenly I got brave, after all I was the host. I was wear slides. I kicked them off, dropped my shorts, revealing that I had no underwear. And then naked I crossed the room, flipped the futon open and jumped onto to it, landing on my back, my arms stretched to the sides.
"Nice equipment," Pam said, and took off her short skirt. Her outfit now looked pretty tame, the jersey top and matching bikinis, but what was exciting was her legs that reached from her crotch to the floor, a distance that seemed to be six feet.
Lando whistled, she waggled her backside. Lando quickly dropped his lower coverings and reached out to help her out of her top.
"Hey Lando," she called, "I never saw you naked. You also have pretty nice stuff, all tan and funky. Hey, I think you're getting hard already. And look over there at Jesse, he's erecting a pole. Anybody got a flag?"
"Make room for me, pull your long arms in," Lando said, stretching out leaving room between us for Pam. Pam left her panties on and crossed the room, her tits shaking like Jello. My hands itched to sound each of them and pass a thumb over her prominent nipples.
She lay down between us. Lando immediately at half rose and pressed a wet kiss on the nearest nipple to him. Pam sighed, "Thanks, I needed that."
Lando motioned for me to take a breast, the one near me. I cupped it in my hand and leaned down and licked it. That brought a bigger sigh.
I could see that Lando's prick was pressed against Pam's hip and I realized mine was too, in fact I had left a tiny trail of pre cum on her hip. The two of us continued suckling away blissfully, like two calves at the teat. We all hummed.
Again I decided to take the lead. I slid down and put my lips against the prominent mound of Pam's vagina. It felt warm and there was a line of moisture where the outer lips were. She smelled heavenly, mossy and girly. She was easily ignited because I just got close and breathed on her outer lips and they opened magically and revealed the red/pink wet pussy interior, more of her heady scent wafting into my nose, making me dizzy and horny. I leaned down and pushed my tongue out and inserted it into her cunt. She began a musical chant telling us just how to do it. Lando put an arm over my shoulder and hugged me in brotherly admiration as I began sucking and licking her with all my inventiveness. I found her clit. "Uh, oh," she said cutely. "I think he's got it." But then could hardly finish the statement as her eyes rolled up and she coasted into a nice short cum. "You're innocent looking but you're a devil with forked tongue, or at least long tongue. Don't stop, I've rested enough, resume your meal."
This time I rapidly flicked her hot button over and over again. She was bucking and crying out. I think she was having a continuous orgasm. Suddenly she pushed me away. "Lando, get busy, put your tan boy cock in me. I want to feel it filling me."
Lando roughly pushed me aside and lifted her legs to his tan hips and rested his cock head at her opening. She pushed forward as he did and he entered her to his pubes. "Oh shit, this is what I've been needing," Lando called out. "It's going to take all I got to keep from cumiing, you are sooo hot."
I stood back watching his strong muscled ass clenching and unclenching as he fucked and bucked, He turned around and saw me staring at it. "Jes, don't be a weeny, I owe you, fuck me."
That was all I needed to hear. With a cry of passion I inserted my prick in his slightly hairy hole. I pushed and the head went in. He let out a howl of pain and excitement. "Go ahead, I want to feel your pubes against my ass."
Pam knew what was going on. "You guys are the sexiest kids I have ever been with. I love that you don't mind trying out some boy/boy things."
I hardly heard her, my head was whirling in pleasure. Faintly I could hear Lando's constant moaning and crying. I heard him say, "Pam, your orgasm is pulsing against my prick. I think I'm done for. Get ready to be hosed."
I could see that Lando's hips froze as he began to slightly thrust and croon his cum. His vibrating inner ass worked on my cock like a mechanical vagina, almost beating my cock as I thrust and suddenly called out my own cum. There three of us were sure noisy, but we enjoyed the pleasure/pain of our cums. It took a long time for us to get back to Earth. Pam was the first to talk, after clearing her threat to talk. "Hey guys, did you like man to man sex, or did you prefer little old me?"
I answered, "Lando's ass is excellent, but your cunt tops it I bet. Next time we'll do it differently but I don't think I have Lando's nerve to take a cock in my ass. Maybe Lando and I could sexiy-nine and you could do some improvising with our asses.
"Ooh, ooh," Lando said. "I agree, gay is good, cunt is better. But maybe gay is good only with you Jesse, my man."
We never go to that three-some. I never had sex with Lando again. School started in the fall and we lost track of each other. Opportunities for gay sex came in my life from time to time, but I remained a cunt man.
End of story. A lot of this is true.