Gary's sexual history (long)

"All right, Gary," Dr. Rubin said. "It's time for your sexual history. Nurse, will you hold Gary's penis while he answers?" Josh Rubin sat down in a chair across from Gary. With the doctor wearing no pants, his own half-erect cock stuck out from below the ends of his white doctor's shirt.

"Yes Doctor," Sonia said. She curled her warm fingers around Gary's shaft. "Medical histories don't have to be boring, and we want you in the right frame of mind," she said to Gary, and gave his penis a squeeze. With Sonia sitting next to him, he could look right down her over-tight nurse's uniform and see the top of her large breasts squeezed together practically under his nose.

"All right, Gary," Dr. Rubin said. "I'll be asking you questions about your sexual experience with different behaviors, with yourself and with other people, women or men. Please answer everything you can. If you need to stop and take a deep breath, that's fine."

"Okay," Gary said.

"How many times a day do you masturbate, on average?" Dr. Rubin asked.

"Two or three. Almost always at bedtime. Sometimes in the morning while I'm still in bed or in the shower. And pretty often when I get home from work or classes."

"What happened the first time a woman touched your erect penis?" Dr. Rubin asked.

Sonia squeezed her fingers lightly on Gary's shaft.

Gary laughed out loud. "I came right away," he said. "I'd been making out for, like, an hour with Kim."

"You don't have to give any names unless it helps tell the story," Dr. Rubin said.

"Oh, right," Gary said. "And she put her hand in my pants and touched me, and it was so exciting I just shot in her hand right away."

"How many women have touched your erect penis?" Dr. Rubin asked.

"I guess..." Gary counted in his mind. Kim, Meg, Sharon, Bernie, and Sonia. And, wow, Bernie's mom Joyce, right. "I guess six, hold on." He turned pink. "Eight." He had been nude in the sauna with Mom and his sister Lil and when he popped an erection, Lil had grabbed his penis to tease him. Mom had played along for a second too. Then Dad had come back, laughed, and put more water on. He didn't think much about it at the time. Oh, and Miss Wilder, Peter's piano teacher. "No, nine!"

Sonia squeezed his cock encouragingly.

"Have you reached orgasm more than once this way?"

Gary thought of a night on his front doorstep, Sharon's hand down his pants, her tongue in his mouth. "Yes," he said.

"Have you done this in the last month?"

Gary smiled, thinking of Bernie squeezing his cock with a big cheesy grin on her face. "Yes," he said.

"Is it something you'd like to do again?"

"Does my cock come up in the morning?" Gary asked. "For sure. Sorry Doc," he apologized for his words.

"Answer however you like, Gary," Doctor Rubin said.

"What happened the first time a man touched your erect penis?"

"My friend and were just kind of playing around. Not that much, actually."

"How many men have you done this with?"

"Um, just, well, four I guess." His friends Peter and Bobby. And Stuart and Trent from the beach crowd.

"Have you reached orgasm this way?"

"Yeah."

"Has a man touched your erect penis in the last month?"

"Um...yeah," he said. He had gotten together with Stuart to pick up the Super Surf Van before Stu left for his overseas trip, and stuff happened. Hands were the least of it.

"Is it something you'd like to do again?" Dr. Rubin asked.

"Maybe, I guess it's OK," Gary said. "It's kind of fun touching another dude's cock, like, someone you know already, like you know them a special way. But you don't want to know everyone like that."

"What happened the first time you touched another man's erect penis?"

"The same, playing around with my friend."

"How many people have you done this with?"

"The same, just four guys."

"Have you or your partner reached orgasm this way?"

"Oh yeah," Gary said. He remembered when he and Peter were jacking each other, Peter shooting through Gary's fist, Peter's hand going so fast over Gary's cock head as he got off.

Sonia gave his penis a squeeze and a little rub to stiffen it.

"Have you done this in the last month?"

"It's actually been a while... Wait. Yeah, I have," Gary said. Stuart again.

"Is it something you'd like to do again?" Dr. Rubin asked.

"I'd like to get together with my friend again sometime," Gary said. "That was fun. But not just anyone, I mean I don't go looking for it."

"What happened the first time a woman touched your penis with her mouth?"

Gary laughed. He thought of his first time with Sharon. "It was kind of a disaster," he said. "It felt sort of good for a while, but we were both too drunk, especially her, so it never got anywhere really."

"How many women have touched your penis with their mouth?" Dr. Rubin asked.

Gary raised his eyebrows. "Three," he said. After Sharon, there had been Sonia. And Bernie.

"Have you reached orgasm this way?"

He smiled. "Oh yeah," he said. He thought of Sharon again. "And the first girl got it right the second time. But I've had better." His cock jumped in Sonia's hand. The doctor's wife had sucked more than one out of him, and she was MUCH better than Sharon.

"Have you done this in the last month?"

"Yes," Gary said. Sonia smiled and squeezed his penis gently.

"Is it something you'd like to do again?

"Do I like ice cream?" Gary asked. "Yeah."

"What happened the first time a man touched your penis with his mouth?"

"I had come back after swimming with my friend, and we were changing, he asked me if he could touch it. I said sure, we'd touched each other before, and he asked if he could try sucking it. It was kinda fun, but we didn't get very far."

"How many men have touched your penis with their mouth?" Dr. Rubin asked.

"Three," Gary said. His friend Peter, and Stuart and Trent.

"Have you reached orgasm this way?"

"Yeah." Peter. And Trent.

"Has a man had his mouth on your penis in the last month?"

Stuart had sucked him hard that night before his trip. "Yeah," Gary said.

"Is it something you'd like to do again?

"I don't know," Gary said. "It really depends."

"What happened the first time you touched another man's penis with your mouth?" Dr. Rubin asked.

"We were just messing around to try it out. Not that much, actually," Gary said.

"How many men have you done this with?"

"Just a couple of guys," Gary said. Peter Walker, of course. And Trent a couple of times.

"Has your partner reached orgasm this way?"

"Yeah," Gary said. Peter. Trent. Their moans, their bodies stiffening, the hot slick juice spurting into his mouth.

"Have you done this in the last month?

"No."

"Is it something you'd like to do again?"

"Maybe," Gary said. "I'd do it for my friend P... Yeah, my friend." Peter.

Sonia gently squeezed his cock.

"What happened the first time you touched a woman's vulva?"

"We were making out, and she put my hand in her shorts." Gary said, thinking of a warm summer night with Kim. "It was really great. She kind of rubbed up against my finger and I think she came."

"How many women have you done this with?"

"Mmmm," Gary said. His girlfriends, plus Sonia. Sharon's friend Jade Pryor. Betsy Wilder. Joyce. "Eight."

"Have you or your partner reached orgasm this way?"

"Yeah, Sharon always got off, and..." Gary said. "Oops. Yeah, anyway. And more often lately. I think I'm getting better at it."

"Have you done this in the last month?"

"For sure," Gary said.

"Is it something you'd like to do again?"

"Every day of my life," Gary said.

"What happened the first time you touched a woman's vulva with your mouth?"

He thought of Meg. "She asked for it one night, and told me what to do." He paused. "She made me shave again." He laughed, and Sonia joined in. "It felt so great to me to kiss her there, I'd been dreaming about it. She finished herself off, but she said I'd done a great job for my first time."

"How many women have you done this with?"

"Hmm. Four," Gary said. "No, six." Not Kim, but his other girlfriends. Jade. Miss Wilder. And Sonia.

"Have you or your partner reached orgasm this way?"

"Yeah," Gary said, and smiled. "They all got off with me. Sometimes they didn't let me finish. And the first time I was with...with one woman, I came just from having my mouth on her." The first time with Sonia had been so exciting.

Sonia laughed and gave his cock a firm squeeze.

"Have you done this in the last month?"

"Sure thing!" Gary said.

Sonia giggled.

"Is it something you'd like to do again?"

"All the time," Gary said. "If I think someone's pretty, I always wonder what she tastes like and I wonder if someone's giving her some good tongue."

Dr. Rubin laughed.

"What happened the first time you penetrated a woman's vagina with your penis?"

"We were sitting in the car outside her house. We'd been talking, and then we were necking, and then we decided to go to the back seat, you know. And we were feeling so wild. I was talking to her about if we were gonna do it some time soon, and she said 'How about now?' and I said yes. So she showed me what I needed to do, and got me inside and it was so GREAT," Gary said. "Though the next day it was all, 'We were so stupid to do it without a condom', at least it wasn't the last time. We lost touch after she went to college."

"How many women have you had vaginal intercourse with?"

Gary thought for a moment. Who had he actually gotten to home plate with? He and Kim had never quite done it. He smiled, still, thinking of her. Meg was his first. Sharon. Bernie. And, well, Miss Wilder. And Sonia.

"Uh, five, I guess," Gary said. Was that a big or a small number? he wondered.

"Have you reached orgasm this way?"

"Right-on!" Gary said.

"Have you done this in the last month?"

"Absolutely," Gary said. "God bless."

Sonia laughed and squeezed his cock.

Dr. Rubin cracked a smile. His half-erect penis twitched and swelled a bit.

"Is it something you'd like to do again?"

"All my fucking life," Gary said.

Sonia giggled. "Men," she said.

"What happened the first time you watched someone else being sexual with themselves or another person?"

"My friend and I watched each other jack off together one time," Gary said, thinking of Bobby.

"How many people have you watched being sexual?"

"Gee, I dunno," Gary said. "A few people. Six or eight maybe?" There was Bobby, and of course he and Bernie liked to show off for each other. There had been that one time with Bernie's mom... Gary swallowed. And then there was the surf crowd. He wasn't sure who he'd seen do what with whom. And Peter banging Miss Wilder. That day, wow.

"Have you reached orgasm watching someone be sexual?"

"Yeah, you know, when you're both doing it for each other," Gary said.

"Have you done this in the last month?"

"Yes, my girlfriend likes me to watch her jill off."

"Is it something you'd like to do again?"

"Yeah, I like it a lot, especially showing off to each other. Sometimes I think it would be fun to watch a couple, I mean like people who love each other, doing it. Or maybe to just listen."

"What happened the first time someone else watched you being sexual with yourself or another person?"

"Well, like I said, the first time was kind of mutual," Gary said. "There was another time, at a beach party, people were getting together and watching each other."

"How many people have you done this with?"

"Same thing I guess, six or eight. I mean, I don't get off on just showing off, really." He swallowed. There was that one time Sharon had kind of made him show off. "Yeah."

"Have you reached orgasm this way?"

"Yeah. Sometimes it was kind of exciting to catch a look off of somebody looking at me, but it was more just being around places where it was OK to watch each other doing it."

"Have you done this in the last month?"

"Yeah, but just with my girlfriend, showing off for each other, you know," Gary said.

"Is it something you'd like to do again, maybe you or both of you showing off for someone else?"

"Maybe," Gary said. "You know, it would have to be the right kind of thing."

"What happened the first time you had sex with more than one person at the same time?"

There had been that incredible afternoon with his friend Peter and his piano teacher Miss Wilder. "I was having lunch with my friend and his piano teacher," Gary said. "I knew both of them already, I had actually taken lessons with her a long time ago but I didn't keep it up and he did. Somehow it came out when we were talking over lunch that she wasn't just his piano teacher any more. And she invited me back with him to see her new place. We played the piano a little together. I was really rusty. And I was gonna go, but I didn't have a ride. And they were kind of looking at each other that way. So I was gonna just go and take a bus or something. And he whispered something at her and she asked me to come to bed with them. And it was like wow, we're doing this. We were making love to her together. And I watched him getting on, going into her. And then me. And everyone was smiling like they were silly."

"How many people have you done this with?" Dr. Rubin asked.

"It was really just that one time," Gary said.

"Have you reached orgasm this way?"

"Yeah, absolutely," Gary said.

"Have you done this in the last month?" Dr. Rubin asked.

"No, it was a little while ago," Gary said.

"Is it something you'd like to do again?"

"Wow, yeah, but I don't know who..." Gary broke off and looked at Sonia and Josh, feeling silly. "Yeah," he said. "If the scene is all right, and, you know, I feel OK about the people."

"What happened the first time another person penetrated your anus with his or her finger?"

"It was a guy, he was sucking me off," Gary said. "And he put his finger on my ass, and just a little inside. I guess it was OK."

"How many men and women have you done this with?" Dr. Rubin asked.

"Just a couple, I mean, a man and a woman," Gary said.

"Have you reached orgasm this way?"

"Yeah, but really 'cause of being sucked," Gary said. He looked at Sonia.

"Have you done this in the last month?" Dr. Rubin asked.

Gary hesitated.

"Yes," Sonia said. "This finger," she said, holding it up.

The three of them broke up in laughter. Gary relaxed and felt more at ease.

"What happened the first time you penetrated another person's anus with your finger?"

"She asked me to do it while we were having sex, because it helped her to come." He'd had a summer fling with Meg, who told him to do it. Meg was good at telling him what she liked. He'd given it a try, and it had worked really well.

"How many men and women have you done this with?"

"Just two, two women." Gary said.

"Have you or your partner reached orgasm this way?"

"Yes, for both women, she came when I had my finger in her butt."

"Have you done this in the last month?"

Gary looked at Sonia, then back to Dr. Rubin. "Yes, when I was licking her."

Sonia caught Gary's eye and smiled. "Licking her vulva," Sonia said. "And her clitoris."

"Is it something you'd like to do again?" Dr. Rubin asked.

"Yeah, sure, if a woman likes it. If it gets her off, that's really great," Gary said.

"What happened the first time another person touched your anus with his or her mouth?"

"He...he licked my ass before he put his cock inside me," Gary said.

"How many men and women have done this with you?"

"Just two," Gary said. "A man and a woman." Sonia did it to him last time. It made him shiver from the intense tickling sensations.

"Have you reached orgasm this way?"

"Um, no," Gary said.

"Have you done this in the last month?

Gary's eyes flicked to Sonia again. "Yes," he said. He gave a nervous laugh.

"It's a normal and healthy behavior," Dr. Rubin said, "Like everything I'm asking about."

"I'd better be normal and healthy!" Sonia protested.

Gary laughed. "Thanks, doc," he said.

"Is it something you'd like to do again?"

"Sure, I guess, if I'm with a woman who likes it," Gary said.

"What happened the first time you touched another person's anus with your mouth?"

"I've never done that," Gary said.

"Is that something you would like to do?"

"I don't know, maybe sometime," Gary said. "I mean, if it was clean and my girlfriend asked me, sure."

"What happened the first time you penetrated a woman's anus with your penis?"

"She was really wild late one night and wanted me to do her in the butt. I tried to be really careful, you know, and she'd done it before, so I guess it wasn't too hard for her. She got off, but I was too tired to make it," Gary said.

"How many women have you done this with?"

"Only two," Gary said. His eyes flicked to Sonia.

"Have you reached orgasm this way?"

"Uh-huh," Gary said.

"Have you done this in the last month?"

"Yeah." With Sonia, three weeks ago.

"And it was good!" Sonia said.

Dr. Rubin smiled. Gary and Sonia laughed.

This time Sonia was the one to ask, "Would you like to do it again?"

"Sure!" Gary said.

"What happened the first time you penetrated a man's anus with your penis?"

"I was in the shower with my friend. We were messing around and he asked me to put it in," Gary said. "I think we used some conditioner or something."

"How many men have you done this with?"

"Just two guys." His friend Peter Walker. And then there was Trent down at the beach.

"Have you reached orgasm this way?"

"Yeah, I got off pretty quick, especially the first time in the shower," Gary said.

"Have you penetrated a man's anus with your penis in the last month?" Dr. Rubin asked.

"Nope," Gary said.

"Is it something you'd like to do again?" Dr. Rubin asked.

"Sure, maybe, once in a blue moon," Gary said. "It's fun, and I get off pretty good, but I guess I wouldn't miss it if I didn't."

"As long as you have a girl you can take like a boy?" Sonia teased, squeezing Gary's penis.

Gary laughed. "Heh, well yeah," he told Sonia. He looked to Doctor Rubin and said, "But even if I didn't have a girlfriend who liked it, I guess it would be okay."

Sonia raised an eyebrow and squeezed his cock head. "Speaking frankly, Gary," she said, "if you don't have a male friend you can put this to, you will be happier if you have a girlfriend who enjoys taking you anally."

Gary gave her a funny look but didn't say anything.

"Thank you, Nurse," Doctor Rubin said. He cleared his throat. "Last question, Gary."

"What happened the first time a man penetrated your anus with his penis?"

"We were up late, you know talking, we'd had some weed, and he talked me into trying it."

"How many men have you done this with?"

"Just one," Gary said.

"Have you reached orgasm this way?"

"Yeah, I came with him inside me," Gary said. "It was pretty weird."

"Have you had a man's penis in your anus in the last month?"

"Yes," Gary said. He flushed pink with embarrassment. "That was my first time." Sonia squeezed and stroked his penis to keep him hard.

"Is it something you'd like to do again?" Dr. Rubin asked.

"I don't know," Gary said. "Not right away. I'd have to think about it."

"That's all my sexual history questions," Dr. Rubin said. "Do you have any questions, or would you like to move on to demonstrating the sexual response cycle with Nurse Sonia?" he asked.