Jack Edwards

So far I’ve received emails after each installment, from at least one reader who said that the previous chapter was much like his own first time experience. Everyone is telling me that these stories bring back memories. These are fun, aren’t they?

The variety of first time experiences surprises even me. Since starting this series, I’ve received several experiences from guys, two of which I found to be absolute hoots. I’m hoping to have them written up before long.

Again, I’m dramatizing these episodes, guys. So if you send me your own, give me some details if you can. Try to remember any of the things that were said or the feelings you had, the smells, the way things looked. Those things can be helpful.

Obviously, if I continue receiving first time experiences from readers, I’ll never get around to writing them all up, so please don’t be offended if I don’t get to yours, if you do send it. And remember, I always suggest you consider posting your own story, if you’re so inclined, and get into writing on your own. Either way, this is turning into a fun project, and I’m really enjoying the experiences you guys are relating.



All my firsts came when I was eleven. My sister Audrey had just turned thirteen and though she gave my parents fits, she and I got along alright, most times. My brother, Eddie, was still fourteen.

We came pretty close together in the birth order. I heard my dad joke once that after three in a row, Mom told him if he got her pregnant one more time, she’d ‘cut it off’. He joked, but I had no little brothers or sisters. I think he got a vasectomy.

Dad used to travel all week. When he got home on Friday nights, he and mom had sex, right off. We all knew it. We could hear them.

Walking past their door one Friday night as they prepared to come back downstairs, I heard my mom talking to my dad.

“We forgot to lock the door again,” she said. “Audrey cracked it and watched us.”

“Well,” dad said with a sigh, “that’s one conversation you won’t need to have with her.”

“Honey, she quit asking me for that kind of conversation a long time ago.”

I hurried along because it sounded like they were about to come out, and I was jealous as hell of Audrey. I’d never of had the guts to try watching my parents, and all I knew about sex was what I heard from other guys. Dad and I never had that kind of conversation with me.

We weren’t real modest in our family, so I did know some of the basic anatomy. When we were younger, I took baths with Audrey. I took even more with Eddie, of course. He and I shared a bathroom. Mom called it the “boys’ bathroom” and we were supposed to keep it clean.

I saw Eddie naked, plenty of times. At eleven, with my own cock and balls beginning to grow, I was endlessly fascinated with Eddie’s adolescent equipment; it looked huge. I tried to catch him naked whenever I could, and once I caught him with a hard-on sitting on the john. I was too dense to realize he must be ‘jacking off’ as I’d heard it called. I just knew the glimpse of it before he slammed the door on me was awesome.

Eddie and I wore underwear to sleep in, colored briefs, mainly, and we wore nothing else around the house in the mornings and at night if no one else was around. More than once, I suspected Eddie had left-over wood in his. Dad made an occasional appearance in tidy whities, usually with a t-shirt. Mom sometime came out of their room in her panties and bra when she was looking for something, and I’d seen her, even recently, in a nightgown that let her tits show through… though after she caught me staring, she put on a robe.

Audrey wore only panties and t-shirts to sleep in, and wore them in the mornings and evenings if no one was around. Until that fall, she seemed about as sexy to me as a bad cold, but lately, I’d noticed her breasts and figure, and had managed a few looks up her legs when her sleep t-shirt rode up.

Mom and dad usually had sex again on Friday nights, when they went to bed for the evening, and that’s why they almost always slept in until mid-morning on Saturday… well that and they sometimes had sex again Saturday morning.

Eddie was usually up late with his buddies Friday night and often had one or two sleep over, so he always slept in, unless he slept in over at one of their places. Audrey and I were both early risers. We’d each tried to be first up on Saturday morning to get control of the TV.

On Saturday morning, there were boys’ shows and there were girls’ shows. The boys’ shows were like, perfectly targeted for eleven-year-old boys and the girls’ shows worked okay for thirteen-year-old air-headed girls like Audrey.

Our TV tuner was a pain to use without the remote, so that particular Saturday, I had it firmly clasped in my hand, ready for a Transformers vs. Smurfs war when Audrey showed up. I had just lain back on our leather couch with a banana in one hand and the TV remote in the other, awaiting the start of my program, when she made her appearance.

In fact, I had just juggled the remote and the banana so I could scratch. For the previous couple of months, I had found immense pleasure, scratching my balls. They hung loose and low, now, and they were shaped like eggs, not like the marbles of a little boy. I wasn’t sure when or how it’d happened, but it had, and it felt good to feel the way they rolled in my scrotum.

There was the problem, of course. Scratching my balls usually gave me a hard-on. At eleven, almost anything gave me a hard-on. So I quit scratching before Audrey showed up. Wearing nothing but briefs, there’d be no hiding my dick if it got any harder. I left my rubbery semi pointing up my belly to go soft.

“Give me the remote,” Audrey said, coming into the den. “You got to watch Transformers last week.”

“And I’m gonna watch it this week,” I said, chewing a bite of a banana. “I got here first.”

She came up beside the couch and extended her hand.

“Forget it!” I told her, holding the remote over the back of the couch.

Audrey climbed on, straddling my hips to reach for it.

Keeping it behind the couch, I moved it away from her. She reached farther.

Her panty-covered crotch hovered so low over my own, I could feel her body heat, and with a mind of its own, my eleven-year-old dick began stiffening up all over again, instantly. She reached farther for the remote, and I took it from behind the couch and held it, and the banana, above my head, thinking that it’d draw her forward from almost sitting on my dick.

It had the opposite effect. She sat down into my lap, exasperated.

Her eyes went wide. Her cunt had landed squarely on my upturned erection.

I froze. Looking down my belly, at her in her loose t-shirt sitting astride my briefs, I looked naked. That only made me harder.

Her eyes narrowed and she wiggled her bottom.

I gasped.

“You little bastard!” she exclaimed with a hiss. “You’ve got a boner!”

I swallowed hard. What was I going to say? She had me. And actually, I wasn’t anxious for her to get up.

Her eyes narrowed even more. “Give me the remote or I’ll make you sorry.”

I stretched my arms even farther.

She cocked an eyebrow. “Oh?” She rocked her hips forward and back and her cunny rubbed up and down the underside of my shaft.

My breath caught, and my mouth dropped. For an instant, so did hers, and her eyes went all unfocused. Her cheeks turned red.

Her eyes refocused on mine. “Give me the remote, Jere,” she said, not sounding nearly as threatening. She rocked her hips again.

I shook my head back and forth, holding the remote far above my head.

Her jaw set and she spread her knees wider, settling more squarely on me. “I’m serious, Jere,” she warned, grabbing my shoulders. She didn’t sound all that serious to me. She sounded like she might not want me to give in. I certainly didn’t want to.

Flattening her cunny on me, she ground and rocked. “You asked for it!” she said in a low voice that wasn’t nearly threatening.

She rocked her hips, watching my face. I looked away. I looked up. I looked anywhere but at her. I started lifting my hips. I couldn’t help it. Barely thinking about it, I dropped the banana and remote over the end of the couch and grabbed the sides of her thighs. She had slender legs, and very smooth skin.

I’d never even had a dry orgasm. I had no idea what an orgasm was, really. I just wanted Audrey to keep doing what she was doing. I held her thighs and ground up with my dick under her.

And suddenly, something was happening, and I didn’t know what.

“Ah! Ah! Ah!” I gasped and Audrey bent over me, covering my mouth with her hand. But she didn’t stop rubbing on me. I grabbed at her bottom, thrusting up instinctively, and felt like I was peeing myself, but it felt way, way better than peeing, and it came in squirts.

With her hand over my mouth, she pressed her forehead on mine, and I heard her moan softly, two, three, four times.

She slowed and took a deep, ragged breath.

Without a word, she climbed off me, and left the room.

I propped up on my elbows and looked down at the front of my briefs. They were wet; really wet. I’d had my first come.

I went to my room to change, and I didn’t see Audrey until lunch, when she ignored me.

I wondered if she felt funny about what we did. I did. I mean, she was my sister after all. And I still wasn’t too sure what had happened. However, one thing I did know. I wanted it to happen again. Unfortunately, all week, Audrey acted like nothing had happened, and then she slept over at her friend’s house that Friday night.

It occurred to me that a guy sitting on my boner the way Audrey did, could work about as well. I thought about my friend, Tyler.

Tyler and I had been best buds forever. We’d even talked about sex. I began thinking that if I could just straddle him like Audrey did me, and wiggle around on him, he’d get into it like I did and maybe do the same for me. I thought about it. I planned it out. I daydreamed about him sleeping over and us being in our underwear for bed and me getting on top of him.

The following Wednesday afternoon, we were at his house, and he was lying on his back, reading Sports Illustrated. We were in jeans and t-shirts, not just underwear, but Tyler was twelve already, and his cock and balls were bigger than mine. The front of his jeans pouched out with them. Looking up his legs, the mound at the front of his jeans stood like a little hill.

My mouth grew dry. I was scared to try it, but my cock wasn’t; it was growing hard. Swallowing, and steeling up my courage, I climbed astride Tyler’s hips and sat on his mound.

“Oof!” he said, sitting up and pushing me off. “What the hell? Geez, Jere, if you wanna wrestle, don’t squash my balls first!”

He rubbed his balls, which didn’t calm my excitement at all. Then he rolled over onto his stomach, and that was that.

A night or two later, I glanced into Eddie’s room, and he was lying on his back, on his bed, talking to his girlfriend. He was in only his underwear, and I could tell he had a boner; no doubt about it, especially when he scratched.

I hadn’t thought about trying anything with Eddie, but I did then. Returning quickly to my room, I shucked my shorts and returned to Eddie’s doorway in only my underwear, hurrying before I could sprout wood.

He was so busy on the phone, he barely noticed as I climbed up onto the bed. This time, I was going to be careful not to sit on his balls. I quickly climbed over him, straddling his middle, and sat down on the underside of his boner with my ass neck [perineum].

He paused, mid sentence, his eyes up on the ceiling. I rocked my hips and his eyes sort of glazed over. He turned all red like Audrey had. All of us in our family have really fair complexions and our cheeks turn real pink when we get excited. I learned that.

I wiggled some more, my dick almost fully hard. But now Eddie frowned and grabbed my hips to stop my wiggling. He held the phone to his chest. “What the shit are you doing, Jere?”

My face grew hot. I hadn’t thought about saying anything. I just thought he’d like it or not.

“I wanted to ask if I could borrow your pellet gun,” I told him.

“No! And get off me.”

Reluctantly, I climbed off him, trying to hide my boner.

“Jere,” he called as I headed for the bathroom and my room on the other side. “Turn around.”

I glanced back over my shoulder at him.

“Turn around,” he repeated.

I covered my crotch with my hands and turned around to face him.

“Drop your hands.”

I frowned.

“Drop ‘em.”

I dropped away my hands. After all, I could still see his boner in hisunderwear.

“Come here,” he said, waving me over.

I walked up beside his bed.

Holding the phone up to his ear with one hand, he pulled the front of my briefs down with his other, exposing my boner.

“Shit!” he murmured into the phone. “Jere’s got a boner. A big one.”

I jerked back, pulling my briefs up. I backed from him, my eyes almost instantly filling with tears.

It’s easy to cry when you have an older brother. I felt so helpless when he picked on me. Perhaps, if he had picked on me more often, I would have handled it better. But he didn’t, and because I held Eddie in a bit of awe, it was easy for him to hurt my feelings. I turned and walked from the room.

Back in my room, I threw myself on the bed. To my eleven-year-old mind, my reputation had been ruined for life. Eddie had told the world I had a boner.

A few moments later, he came into my room and sat down on the bed beside me.

“Why’d you get upset?” he asked, laying his hand on my bare back. He rubbed it gently.

“You told Stacy I had a big boner,” I said.

“So?” he said with a chuckle. “Girls like big boners.”

I glanced up at him, skeptically. “Is yours big?” I asked. “Does Stacy like it?”

He frowned. “Stacy hasn’t seen it. Here. You tell me.”

Eddie lay down on his back beside me and pulled down the front of his briefs. His dick was thick and rolled up onto his stomach. Holding the front of his briefs with one hand, he closed the other around his dick and pointed it up at the ceiling, giving it a slow stroke.

“I’ve only seen one other boner,” he said, “besides yours and mine, that is. David Reilly and I jacked off together a couple of times. Mine’s bigger.” He glanced at me. “Roll over. Let’s see how big yours is.”

I rolled to my back and scooted over beside him. Like Eddie, I pulled down the front of my briefs with one hand and held up my dick with the other. Mine had started to soften, too, so I tried to stroke mine like Eddie was stroking his, wrapping my hand around it.

“No,” Eddie said. “Use your thumb and fingers like this.”

He shoved my hand over and closed his thumb and two fingers around my shaft, using the two fingers on the underside of my shaft and the thumb on top. “When yours gets longer, you can use your whole hand better, but start out like this for now and it’ll work better.

He stroked up and down my shaft while I held my head up, watching wide-eyed.

“Feel good?” he asked with a grin.

I nodded, my mouth hanging open.

He stroked my dick and watched my face. “You’ve never jacked off before, have you?”

I shook my head.

“Here,” he said, taking my hand. He placed it on his dick. “You do me and I’ll do you.”

We kicked off our briefs and I closed my hand around his cock. It felt huge and hot. Eddie repositioned my hand and showed me how to do it right.

“You spunking yet?” he asked.


“You shooting cum yet?”

I nodded. “I just started.”

He grinned. “Cool. I’ll make you shoot. You make me shoot.”

We leaned up toward each other, trying to keep a good angle.

“Jere,” he murmured, “back when I was on the phone, why were you trying to sit on my hard-on?”

“I thought it might feel good,” I said.

Eddie bit his lip. “We can try it if you want.”

I nodded. “Okay.”

I sat up and Eddie lay back. His dick lay up his belly all thick and pink looking. I threw my knee over his waist and sat down on his upturned cock, pressing it back up against his belly. Eddie rested his hands on my legs, and I started rocking forward and back on him.

“Ummm,” he murmured with a sigh, his eyes drooping.

It felt good to me, too; his thickness down under the very root of my cock, under my balls. The very end of his cock extended past my draped scrotum. My cock pointed up over his belly. And I wondered what it would feel like if I backed my hips a little and rubbed my dick with his.

I tried it. I put my hands on his shoulders and backed my hips, leaning forward over him so that my dick rubbed with Eddie’s. He grabbed my bottom and moved me around on him, and we kept moving till he came bare seconds before I did. He was still squirting cum on his belly when I started squirting mine. We watched, not breathing, as our two moving dicks spewed cum between us.

“Wow,” I murmured.

“Awesome,” Eddie agreed.

I sat back up onto his lap.

“Get a washrag,” Eddie said, dragging his fingers through our cum.

I ran into the bathroom and returned with a washrag, climbing back astride his hips because it felt good to have my balls and dick rest on his. Then I used the rag to clean up his chest and tummy.

“You can get off now,” Eddie said. “You’re making me hard again.”

I knew what he meant.

The very next evening, Eddie didn’t even bother calling his girlfriend. He motioned for me to follow him up to our rooms after supper and closed the doors.

“I’ve been thinking about what we did last night, and I have another idea,” he told me. “Wanna try it?”

I nodded enthusiastically.

“Great!” he said, unbuttoning his shirt.

I pulled off my t-shirt, and the two of us stripped naked. By the time we got our briefs off, we were both hard.

“Let’s start like last night, and I’ll show you my idea,” he suggested, getting up on the bed and rolling to his back.

I quickly straddled his hips and leaned forward onto him so that our cocks lay side-by-side up his belly. Then I started pumping my hips.

“What I thought about was, like, rolling to our sides, okay?”

I nodded, and we tried rolling onto our sides keeping Eddies hips between my thighs. He held my sides and I held his shoulders and we pumped a little, but it didn’t work as well.

“Let’s roll again with me on top,” Eddie suggested.

We rolled again, still keeping his hips between my legs so that as he rolled on top our boners were pressed between us. Then he lay down on me, grabbing my shoulders and I wrapped my arms around his neck. He started pumping his hips.

I loved it. Eddie was lean and athletic and his body felt great lying on mine. The naked skin of our bellies and chests and legs, pressed and brushed and rubbed. The side of his face against mine felt… intimate. As we got into it, I hooked my heels behind his thighs and felt over his back with my hands. I could feel his muscles moving.

“This is a lot better,” I told him.

“Yeah,” he said in a thick voice. “I like it, too.”

He slid his hands down under my butt, clutching it as he ground his dick down against mine. I held on to the backs of his shoulders, mainly gasping and letting him do all the work.

“I’ve been thinking, Jere,” he murmured. “We can try lots of things.”

“Yeah,” I murmured back. “But I like this a lot.”

“Yeah,” he said, rubbing the side of his face against mine.

My bed rocked, making faint noises that wouldn’t be heard outside the room. It didn’t take long for both of us to come. And then Eddie just sort of rested on me, and I liked the feel of him there with his weight between my legs and on my tummy and chest. I felt over his back with my fingers, admiring his muscles.

Eddie and I wound up doing lots of things together in the months that followed, but I have to relate what happened with Audrey.

I was very late coming down that next Saturday morning because I snuck into Eddie’s room and rubbed with him, then fell back to sleep under the covers with him. It had been a couple of weeks since Audrey had rubbed on me, and though the memory was vivid, things were pretty much back to normal between us. I decided we probably would never do that again, and we certainly couldn’t that Saturday because everybody was up.

Something happened the next Friday evening, though. Mom and Dad went out on a date and Eddie was on a sleepover with his buddies, so it was just Audrey and me at home.

I was on the couch in my underwear watching TV, head propped up at one end. I’d lost track of where Audrey was, until she came in the room in her sleep t-shirt and went over to pick up a pillow off the floor. When she bent over to pick it up, her butt was toward me. Her shirt came up, and I could see she wasn’t wearing panties. I could see her pussy lips between her legs.

She remained bent over for several seconds, and I stared, getting instantly hard. Then she stood up with the pillow and turned toward the couch. As she headed to the other end of the couch, hugging the pillow, I saw her glance at my briefs.

She sat down, hugging the pillow to her belly, and her eyes darted to my briefs again. I had a boner, and it was lying straight up my belly. Her eyes rose to mine.

“Give me the remote, Jere,” she said quietly.

I shook my head, holding the remote back up over my head with both hands.

Silently, Audrey got up from the other end of the couch, setting the pillow aside. Watching my eyes, she knelt astride my hips, and then lifting her shirt, she settled her bare cunny on my upturned dick. I saw her black pubes before she lowered her shirt again.

She closed her eyes and ground down onto me. I dropped the remote over the end of the couch and onto the floor, and grabbed the sides of her legs.

Audrey’s legs back then looked almost like mine with long slender muscles. I rubbed the sides of them, and she started rocking forward and back. With my head and shoulders propped up like they were, it was sort of natural to slide my hands up her sides under her t-shirt, and onto her boobs; I wanted to feel her boobs.

They were firm, with very smooth skin. She fell forward onto her hands on my shoulders and looked down at me, our eyes meeting as my fingertips found her nipples and I discovered that they were all tightened up and pointing.

Her eyes drooped, and I ran my fingers lightly over her nipples. “Does that feel good, Auddy?” I asked.

She nodded. A couple rocks more, and she stopped. She backed down my legs and pulled down my briefs. I felt the air on my boner and balls. She pulled my underwear all the way off and then sat on my legs, looking closer at my middle. She lifted my balls on her fingers and ran a fingertip up the underside of my cock. She closed her hand around it and squeezed. She aimed it up at her face, and I almost laughed, thinking she was like, looking down a gun barrel.

She held my dick up at an angle and slid forward to rub her cunny against the underside again. She let go of my dick and rubbed it down onto my belly with her cunny, while at the same time, she pulled off her t-shirt. I remember, her pussy was really, really wet, flattened over my dick.

She sat looking down at me, and I thought she was absolutely beautiful, naked.

Audrey took my hands and put them back onto her boobs, and then leaned forward onto her hands again, placing them on my shoulders.

I came first by a little bit, squirting up my belly, but she kept going until she came, too.

We did it again the next morning; Saturday morning. And again the next Saturday morning. About the fifth or sixth time we were doing it, Audrey was playing with my dick, rubbing the crown up and down in her crevice, and she moved forward.

“I want to see how it feels,” she said, “just putting the end of it in.”

Next thing I knew, I felt her hole slide down over the end of my dick. I moaned… loudly, and she froze there, biting her lip, making microscopic movements with her hips. She worked me in little by little until I felt something against the end of my dick. Suddenly, she just sat down, my cock broke through her hymen, and Audrey’s hole slid all the way down my cock.

She tensed and sat bent over for a few seconds. Then she rocked her hips forward and back. I clutched at the sides of her legs and moaned again as my cock moved inside the warm sheath of her vagina. She rocked harder and faster. She leaned over me and I hung on to her breasts, caressing them.

“Don’t come inside me,” she whispered.

It was only a couple of minutes later that I squeezed her breasts and lifted my head. “Auddy, I’m getting ready to shoot.”

The warning only seemed to make her more excited. She started rocking really hard.

I tried to hold back, but what she was doing was too much. I cried out, sitting up. When I did, she hugged my face between her breasts and I hugged her, and she went crazy rocking in my lap. I gasped and whimpered because my crown became sensitive after coming.

She finished. She let go of me, and I lay back down.

“Shit!” she said, her eyes dropping to mine. “You better not have knocked me up,” she warned, climbing off me.

It scared her, and we didn’t do anything for almost six months. I was still doing things with Eddie, though. Audrey guessed it, but begged me to not ever say anything to Eddie about what she and I had done together.

Summer came, and we went swimming at the beach. Out in the water, Audrey and I got to wrestling, and I got hard, and we felt each other up under the water.

We had a two room suite with my parents in one room and Audrey in the other. Eddie and I slept on the couch and a rollaway. That night, I waited until everyone was asleep and then snuck into Audrey’s room.

Audrey and I had sex pretty often after that, for almost two years, and we still do on occasion, even though Audrey’s married and I’m living with my girlfriend. Eddie and I quit doing things when he started having sex with girls. That is, except for the summer after I graduated from college and before I went to grad school. I lived the entire summer with Eddie in his apartment. He was between girl friends and so was I, and well, we had a great summer.


My apologies to any puro gays for the appearance of a girl in this series, though brief. It’s the only "first time" story like this that I had permission to post, so far. If I get another one or two, I’ll split them out to a bi section Book of Firsts.

For those of you wondering, "Eddie" is actually a combination of two rubbing stories. The guy who started with his sister told me that once they got going, the two of them rushed home every day after school for sex, for months, and I thought some of you would find it a hot story.

There’s a reason I combined the two stories, and it leads me to consider making a request, since readers have started sending me their stories… In the past, I’ve had a few female readers from time to time (a number hang out here at Nifty). I’d be interested in any female first time experiences as well. Remember, though, that this is a gay/bi site, so gg, or gbb or ggb would be easier to work in.

I've enjoyed your emails tremendously, guys. As you know, reader emails are the only pay we Nifty writers receive. My email address is jnuanced@gmail.com.