We were the best of buddies, all eight of us. We lived within three blocks of each other, went to the same grade school and high school. Greg, Joe, Larry, and myself, John, plus the four girls, Marsha, Cindy, Melissa, and Barb. Mostly we gathered at my house since we had a nicely finished basement. There were no secrets among us. The girls openly gossiped about other girls in school and which boys were cute. We in turn candidly evaluated other girls.
When the girls started maturing, their talk included the latest developments in breasts. First bras.
It was all very innocent coming-of-age. We boys were a little more circumspect about our changes. Voices that were erratically changing, one moment like the boys we were, the next with croaks and high pitches. No one mentioned penises until one day when the girls were in a particularly giggly mood.
"We'll show you ours if you show us yours," Cindy declared. They had been plotting for a week. All four had apparently developed breasts and wanted to show off. "Come on guys," Barb chimed in. We just sat there, looking both surprised and dumb. Barb looked at the other girls, shrugged, and lifted up her top. No bra! And two smallish breasts with erect nipples. "What do you think, guys? Each week they seem a little bigger. Bet you'd like to touch them. Sorry," as she pulled down her top.
"Guys, three more to see. All you have to do is show us your cocks," Cindy persisted.
Larry was the bravest. He stood up, unfastened his pants. His underwear was sticking out in front. "Look, Larry has a hard-on," Barb exclaimed. "Did I do that? Poor thing. Come on, pull them down."
He was beet red but having gone this far was determined to continue. His cock jutted out at a 45-degree angle. The girls stared at their very first erect cock. "Look, Melissa, it's all red. Does it hurt?"
"No," as he quickly pulled up his shorts and pants.
"OK, I'll go next," Cindy said as she unbuttoned her shirt. Again, no bra. Her breasts were about the same size as Barb's. "John, I want to see your cock." At least I wasn't first. My cock popped out, hard as a rock. I was pleased that it was noticeably bigger than Larry's. Marsha and Melissa were next, followed by Greg and Joe.
That was the end of the exhibitions but certainly not discussion. The girls wanted to know how often we got hard-ons. What did we do if it happened around people? That sort of thing.
All through high school we remained just friends. But our sexual discussions became more prevalent
Once afternoon after classes Cindy was the first of the group to arrive at my house. "John, I want to ask you something," she began. "Yeah, go ahead."
"Have you ever kissed a girl?" "Of course, I've kissed my mom and sister many times."
"No, I mean really kissed a girl, a girlfriend?" "No, I've never had a girlfriend. All four of you are my friends."
"Well, I've been wondering what it's like to really be kissed. Would you kiss me?" Cindy put her face close to mine. "Kiss me, John."
I kissed her lightly and briefly on the lips. "More, John." I pressed my lips to hers and she pressed back. Our kiss lasted maybe ten seconds. "That was nice. Thank you. I think with some practice you could be a really good kisser." This time she kissed me, hard.
The doorbell rang and the rest of our group showed up.
************
"Can I come over tonight?" Cindy asked. "Sure, what's up?"
John, we have been friends for, what, ten years? Back to 4th grade. You and the other guys are my best friends. I have decided that I want to have sex, to give up my virginity. It's something I've been thinking about for months. There's no one I would rather be my first. Would you make love to me? Now?"
I was taken by surprise but not completely. The past few weeks Cindy seemed to pay me more than usual attention.
"I've never done this before," I said. "Me either." I knew the basics, of course. But I didn't want to come across as a total klutz. Guys were supposed to know.
"Do you think I'm pretty?" "Very much so. You are one of the best looking girls in school. I like being around you. I like your smile. And you have a very sexy body. You looked great in that bikini you wore last month. "
We were in my bedroom; my folks were at some show. Cindy stood before me and peeled off her clothes. I sucked in a breath as she lowered her panties.
"Very nice, Cindy. You are beautiful and so very sexy. Did you shave your pussy hair?" "Yes, most of the girls I know are doing it now. Do you like it?"
I quickly shed my clothes and stood before her with my big cock sticking out. "John, remember when you guys showed us your cocks? You were the biggest. I wondered at the time how something that big would ever fit inside a girl. I think it's even bigger now. I want to touch it."
"Oh, it's hard and soft at the same time. And you are leaking out its little hole. Are you getting excited?" We laid on the bed and kissed. I was ready to do more but not sure exactly how.
"Use your hands to massage my breasts. Yes, now play with the nipples. Oh, look, they're getting stiffer and sticking out. That feels good. Lick my nipples. Mmm, nice. Now, John, I want you to play with my pussy. Easy, just rub up and down between my pussy lips. Oh, that feels good! Now find my pussy hole and gently push in your finger. Yes, like that. Now in and out."
She reached down and spread her lips and I pushed in further. "Now I'm ready for your cock. Just go in a little way."
I pushed my cock head inside and held it in place. I wanted to shove it in but Cindy reached down and put her hand on my cock, preventing it was going deeper. Oops, what about a condom, I suddenly thought. As if reading my mind Cindy said she was on the pill. I went in and out, just using my cock head. After a minute or so she removed her hand and I went in another two or three inches.
"That's my hymen. Don't go any deeper for a moment. Let me get ready. OK, push, do it quickly."
She let out a little yelp. I stopped and waited to see what she wanted me to do. "OK, you can go deeper." I kept going for a long time but couldn't cum. I guess I was just too nervous. I could tell that Cindy was not having a good time. "Don't worry about it, John. It hurt some. Next time."
We had sex again the next Wednesday and I thought it was great. We were more comfortable in what was to happen and I was less apprehensive as to my performance. We did the basics, kissing, fondling, missionary position. Cindy winced a few times when I went deep into her. I climaxed but she didn't. Later, neither of us said anything to the others in our group.
Two weeks went by. Cindy arranged for us to get together again.
"John, I had sex with Larry. I wanted to see how another cock would feel in me. Don't be mad at me."
"I'm not, Cindy. We aren't dating. But I am really surprised."
"When you guys showed us your cocks that time, yours was the biggest. Larry, Greg, and Joe were all about the same. Nice, just not as long or fat. The first time you and I made love it hurt. I expected that since I was a virgin. But the second time your cock was so big it still hurt some. I wondered how a smaller cock would feel. Would it hurt the same way? So I asked Larry.
"He thinks he took my virginity, doesn't know anything about us. We did the same things you and I did. It was his first time and he did OK. We promised to keep it a secret."
"Anyway, I enjoyed sex with him more than with you. I climaxed, my first. It felt terrific. Please don't get mad, it's just that his cock fits my pussy better. I still want to be your friend, just like always."
"Oh, I almost forgot. Barb and I were talking. Not about us, not in that way. She thinks you have become really handsome. She has a crush on you. If you approached her in the right way, the two of you might hit it off. Could be your second virgin!"
I had apparently become Cindy's confidant as well as first lover. Sometime later she confided in me that she had seduced Greg and Joe. She was remarkably candid in relating her experiences. She said their cocks all fit nicely and that she enjoyed both times. She said they were still just friends. She did tell them that she had sex with Larry.
Cindy and Larry told our group they were dating. No mention of sex but the guys knew and the other girls guessed.
I decided to take Cindy's advice and ask Barb out on a date. Movie and pizza. We have known each other since 4th grade. So our chit-chat was on a superficial level until the subject of sex came up. Barb said Cindy just told her she had sex with all four of us guys. And that I was her first. Barb was curious about the sex, how it felt, what you did. Cindy was effusive in describing all the details. She even admitted that she liked sex with me but that my cock was too big and hurt. So she tried the other guys and settled on Larry.
"What was it like, John? Did you like doing it?"
"Very much so. I was so nervous that first time that I couldn't finish. And Cindy wasn't satisfied either. But it was our first time. The second time was much better, at least for me. I filled her pussy with my stuff. I enjoyed it very much. But Cindy said my cock hurt her."
"When you first put it in, did you go all the way? Tell me."
"No, I first inserted just the head of my cock and moved it in and out just a little. After a minute or so I pushed it in further but hit an obstruction. Her hymen. She told me to do it quickly. I shoved hard and went in almost all the way. She grimaced and let out a yelp. I guess it must have hurt quite a bit.
"I didn't know what to do next, so decided just to stay in her and not move. But I couldn't stay still and started moving in and out, slowly. Cindy was tense and holding her breath. Another minute or so and she relaxed some. I continued for at least ten minutes. Nothing much seemed to be happening so I just stopped and pulled out."
"We didn't have much to say to each other. Cindy cleaned up and left. The second time was much better and I came inside her. Felt much better then when I jack off. Cindy didn't say much and I decided I was not a very good lover.
"That's not what Cindy told me. She said you were very nice and gentle but your cock hurt too much. That's why she wanted to try the other guys."
