Underwear Friends Ch. 03

Mark and I had started a regular relationship. We would see each other in gym class four days a week, and tried to keep it casual. Once a week after school we would go to Mark's house for 'math tutoring', but it was really an excuse for us to indulge in fantasies and have sex.

Mark was from Texas, and the only guy I knew who regularly wore boxer shorts and A-shirts. The rest of us in the small Minnesota high school wore little white briefs and colored t-shirts, and Mark's white boxer shorts with little patterns were an arousing novelty to me.

For Christmas that year, I had asked my mom to buy me some similar boxers instead of the briefs she usually bought my little brother and me. I told her that some of the guys were switching to boxers, and since that's what my dad wore, she understood.

Christmas morning, I tried to downplay my excitement, as I opened a present to find a pack of A-shirts, and two 3-packs of JC Penney boxer shorts. One pack had some modern designs, paisley, plaid and striped. The other more traditional white with little boxes, dots or triangles in blue and red. Mark had some exactly like that!

"I hope those are the right kind, Ray," my Mom commented. "There were a lot of styles, they must be more popular now."

"Thanks, mom. Yeah, these are great."

My 14-year-old brother was surprised to open a present and see his usual 3-pack of briefs and some t-shirts, but also a 3-pack of boxers. They were white with little medallions, shields or diamonds.

"I thought you might like some boxers too, Tommy. I saw another mom looking at them in the boys section."

Tommy shrugged his shoulders. "Sure, mom, thanks."

We finished opening the rest of our presents. I noticed that my mom had bought my father his usual white boxers, but she also picked up a second 3-pack of patterned boxers in his size.

"I thought you might want to try some new designs too, dear. Now all of my men can be in style," she smiled.

"How about you, honey? Did you get some boxers for yourself, too?" my father laughed.

"No, silly, just my usual things. Tommy, " she changed the subject, "open your next present."

I imagined what my mom's new underwear looked like. While searching for my father's underwear a few weeks ago, I had accidentally opened my mom's underwear drawer. There were several pairs of nylon panties in white and pastel shades - blue, pink and yellow. Even after two kids, my mom still had a hot body, and I wondered how she would look in those panties....

Christmas break was soon over, and it was back to school. I couldn't wait to model my new shorts for Mark. We met in the locker room as we changed into our gym clothes. We noticed two other guys in the locker room had started to wear boxers now too. One guy at the end of our locker row was wearing light blue shorts, and another had light green ones.

"Check out my new shorts!" I whispered as I undressed to reveal my paisley boxers.

"Wow, very hot, man!" he muttered in a low voice. "I'm jealous. I didn't get new underwear for Christmas."

"I also got a pack with patterns just like yours - the boxes and diamonds and stuff."

"Can't wait 'til Wednesday, man!" he whispered.

At our next 'tutoring session', I wore the boxers with red and white boxes. As we stripped down at Mark's house, he said, "Yeah, those are just like mine!"

"I brought you a present."

I handed him a bag from my backpack. He opened it to see a pair of my father's full-cut white boxers with a snap front.

"My father got new underwear, too. And my mom threw out some of his older ones. I snuck these for you to keep, since you didn't get any underwear of your own for Christmas." I smiled.

"Thanks, Ray," Mark grinned. He slipped off his own boxers and put on the white ones. They hung very loose on him, and he immediately got a hard-on.

"Now about those bad grades...."

We went to Mark's room, where we had another father/son role-play. He stripped me, spanked me, then fucked me in the ass. It was getting easier and easier for us to pleasure each other, and the anal sex was much less painful now.

I loved to feel his hands on my body, warm and strong. And I liked his firm authority. We played a few times at me being the top, but it didn't seem as arousing as me being the bottom.

I liked him telling me what to do, and following his commands.

After the release, we were lying in each others arms, gently kissing and talking. It felt so good to be able to share our likes and feelings with each other. It was still a huge secret what we were doing, but it felt so good to be together.

"Hey, Mark, how much cum did you put in me? I can still feel it leaking out!" I laughed.

"Hey, it was a long Christmas break, man! I missed you."

"Yeah, but I don't want to leak in my new shorts!"

Mark burst out laughing. "That never bothered you before in your old briefs?"

"Well, no. I always discretely clean out the crotch before throwing them in the laundry. I just hate to leak in my new boxers."

He got off his bed and walked to his dresser. "Here, you can wear my boxers home."

Mark opened his underwear drawer and pulled out his matching boxers, the white ones with blue and red boxes.

"They are a little older, but still look new enough. Your mom shouldn't notice any difference in the laundry. I'll wear yours."

So we began a new game, swapping our matching underwear, and keeping it a secret from our moms. It felt kind of exciting, wearing Mark's boxers, and knowing he was wearing mine. Thinking about how our cocks were kind of touching, even when we were apart.

Sometimes, we would discretely swap in the locker room at school when no one was watching. That was even more hot, especially when one of us would leave some of our fresh cum in them.

Throughout the rest of our senior year, we continued our secret relationship. Mark had casually started seeing a girl on the side, after asking me if it was okay. I liked him a lot, but also liked girls, and wasn't too jealous as long as we still had our Wednesday afternoons.

Mark would share his encounters with Cindy to me. They had started petting, and one weekend she jerked him off in his car. Cindy was pretty horny, and soon they were moving faster on to other things. He told me she was on the pill and loved to fuck with no condoms.

"Ray, you can't believe how good it feels to stick your dick in a pussy! So hot and wet and soft! Cindy squirms like a monkey, man! But she can't give a blowjob anywhere near as good as you can!"

"Ok, now I'm getting a little jealous...."

"I should see if she would try a three-way with you. You game?"

Who wouldn't be?

Mark's mom was going away for a weekend in two weeks. So, he started working on a plan. His mom wasn't crazy about leaving him home alone, especially since he had started dating Cindy. He asked her if I could stay over that weekend, sounding like he wasn't too comfortable in the house alone at night. She agreed, on the condition that we have no parties. My parents agreed to let me stay once they found out that one of Mark's neighbors was a cop.

Mark kept busy those two weeks, avoiding sex with Cindy, and getting her even hornier for him. He mentioned his mom going away and how I was staying over, but invited her over to watch movies. She was a little bummed out that I would be there, but probably thought she could get him away for some action upstairs.

Friday finally came, and Mark's mom left for her weekend away. Mark and I picked up Cindy, and went to his place for pizza and to watch a movie. We had a few beers, and were sitting on the couch.

Cindy was cozying up to Mark, and he was sneaking kisses with her as we watched the movie. She was getting very horny, and whispered something in his ear.

"That would be rude to Ray," I heard him whisper. "He would be alone."

Cindy looked at me and asked, "Ray, would you mind of Mark and I went upstairs for a while?"

"Hey, no problem. Just be quiet about it," I grinned.

"Cindy, go give Ray a big kiss so he won't be lonely," Mark suggested.

She slid over on the couch and said, "Thanks, Ray!" Then took my face in her hands and gave me a big kiss on the lips.

"Cindy, that is so hot! Do that again for me!" Mark commanded.

She crawled up on my lap and planted another kiss on me. Mark came up behind her and gently caressed her breasts. She groaned in delight.

"Cindy, you are so sexy! Your nipples are getting hard. Can Ray touch them?"

She looked a little surprised, but Mark's big smile made her feel all right. She took one of my hands and placed it on her breast. I stroked it and felt her hard nipple, and my dick quivered.

"That is so hot, Cindy. You are driving me crazy! Flash Ray your boobs for me."

"You wanna see my boobs, Ray?"

"Oh yeah, Cindy! I'd love to!"

She leaned back a little, still sitting on my lap, and pulled off her t-shirt and revealing a baby blue bra. Her nipples were clearly erect through the shiny material.

"Reach around the back, hon, and unhook me," she smiled.

How can you refuse an offer like that? I slid my hands around her back and unclasped the bra. I helped it fall of her shoulders, exposing her soft, firm breasts.

"Those are so sexy, Cindy!"

Mark came up behind Cindy and cupped her breasts in his hands. She laughed and gently pulled his hands away. "Later, Mark. Now it's Ray's turn. You're not jealous, are you?"

Our set-up was working. She was so horny, and she was going to let me into their little sex play.

"Come on, Ray, you can touch them. You know you want to," Cindy teased.

So I cupped my hands on her warm breasts, sliding my fingers across her nipples.

"She likes it when you tweak her nipples," Mark offered.

So I gently tweaked and pulled on her hard nipples, twisting them between my fingers as she leaned her head back and moaned.

"Oh god, Ray, that feels so good! You are getting me all wet!"

"Cindy, let him see how wet you are," Mark gently prodded. "You know how much that turns me on."

Cindy thought it over, then climbed off my lap, standing in front of me. She undid her blue jeans and pulled them down. She was wearing matching baby blue panties. Once her pants were off, she spread her legs for me to see a dark damp spot in the crotch.

"Ray, smell how good her pussy is!"

"Oh no, not until he takes off his jeans first. And you too! I'm not gonna be the only stripper here."

So we both took off our shirts and jeans, standing there in just our shorts.

"Hey, Ray, those boxers look just a pair Mark has! Did you know you guys had the same underwear?"

"We found that out in the locker room at school."

"Oh cool. Mark is the first guy I ever saw wearing boxers, and I think they look pretty sexy on him. Now I know two guys. And you look pretty sexy yourself, Ray."

Cindy came up to me and planted another big kiss on me, grinding her body up against mine, so she could feel my cock through the material.

"Mark, do you think you can keep yourself busy while I check out how sexy old Ray is here?"

Cindy slid her hand inside my boxers, and started stroking my cock as she continued kissing me. Her hands were smaller than Mark's, but she knew her way around. She deftly ran it up and down my cock, stopping to cup my balls, then a few slow tugs on the shaft.

"Mmmm, that's a big rod you got there, Ray. Might even be bigger than Mark's. You guys ever compare?"

"We were waiting for the right judge to come along," Mark added.

"Ok boys, show time."

Cindy led us to stand next to each other, then kneeled in front of us. She pulled down Mark's boxers, his shaft flipping straight up. She kissed the head, then ran her tongue up and down the length.

"Mmmm, nice and hard, tastes good. Ray, let's see what you got."

She pulled down my boxers, then kissed my cockhead. The shivers ran right up my spine. Not the same as Mark, but still, oh so good. She licked the shaft, then backed up.

"Ok boys," she called, as she grabbed both of our cocks, and pulled us together, our cocks touching the entire length.

"Looks like Ray is a bit longer, so we have a winner! He gets to fuck me first, Mark, then I'm all yours!"

I couldn't believe my ears! Mark and I had been hoping for this for a long time. Cindy pushed me back to sit on the couch, then stood with her damp panties in front of my face.

"Still want to take a whiff?"

"Oh yeah, babe." I puller her closer, smelling her musky fragrance. I licked at the damp spot, then pulled her panties off. Cindy's pussy gleamed in the dim light, her dark pubic hair matted down with juice.

Mark hugged Cindy from behind and gently turned her around. "I'll help you sit on that long cock of Ray's."

He helped Cindy straddle my lap, her back to my chest, as she positioned her wet pussy over my hard cock. She guided my throbbing meat into her sticky wet lips as she slid down to sit on my lap. Oh god, Mark was right. It felt so good inside her pussy. Warm, wet, soft, feeling her muscles squeeze my iron hard cock.

Then Mark surprised us both, by kneeling down in front of us and ran his tongue from my balls to her clit, up and down, while I was completely inside her. With one hand, he massaged my balls, with the other, he tweaked Cindy's nipples, all the time licking up and down the base of my cock to her engorged clit.

I could feel Cindy start to spasm, her voice squeaking in and out, "Oh oh oh oh oh..."

The pleasure was so intense, I couldn't hold it, and I shot a huge load into her pussy. That seemed to trigger her, as she screamed out and spasmed. I could feel juice leaking out on my lap, and hoped the cop next door didn't hear.

"Oh god, Mark, that was so good! I don't think I ever came that hard before. Quick, your turn now!"

Cindy got up off of me, a bunch of juice dripping out, and sat back on the couch, her legs spread. Mark kneeled in front of her, and slid his hard cock into her messy wet pussy. I could hear the slurping as he pumped her, and in a few minutes he shot his load, and triggered her second climax.

Cindy pushed Mark away, and his cock plopped out. A stream of creampie started oozing out.

"Quick, before the couch gets wet!"

Mark stuck his head into her crotch and began lapping up our combined cum and pussy juice.

"Save some for me, man!" I joined him, alternating how we lapped up the gushing cum soup.

Cindy got so hot watching us take turns eating our cum out of her, she came a third time, pushing out the rest of the cum.

"You guys are the best lovers I've ever had. I never thought two guys would share a girl and not fight about it."

Mark winked at me. "It just worked out, I guess."

We all went upstairs and laid on Mark's bed in each other's arms for a while, making sure to set the alarm in case we fell asleep. Cindy had to be home by 1.

"Mark, can I wear a pair of your boxers home? My panties are so wet and I want to sleep in your shorts thinking of you two tonight. I'll keep it our little secret."

"Of course. Tomorrow you can wear them back over here, and we can help you change out of them," Mark grinned.

"I am so jealous. I really want to sleep here between you two tonight. I was going to suck you both off now. But I suppose with me gone you'll have to wait until tomorrow anyway."

"Yeah, what would we do without you?"