Underwear Friends Ch. 05

During the middle of summer, while my little brother was away at camp and my dad was on a business trip, my mother and I had connected during a period of mutual loneliness. My dad had been having an affair, and my best friend and lover, Mark, had moved back to Texas. My mother and I had a drunken night of sex, that led to a few more exploratory sessions, before we eventually agreed to end things and move on.

Now it was time for me to start college in Wisconsin, a few hours from home. I was accepted late, and on-campus housing was already filled, so I had to find a nearby apartment. There were a number of people advertising for roommates, so I called around and met Chris. He was 19 like me, but his shorter height and skinny frame made him look a few years younger. Chris seemed like a nice guy, and when we hit it off during our first meeting, he offered to let me move in.

It was an upstairs 2-bedroom apartment a few blocks for campus. Our downstairs neighbors were a group of three guys a few years older. I was lucky that there was an extra parking space where I was able to keep my beat up Chevy.

Chris was pretty shy and modest. I would never see him unless he was fully dressed. He wasn't dating anyone, and I decided not to tell him about Mark and me. I wasn't sure if he would accept the fact that I was bi, and since I really needed a place to stay, I kept quiet.

School was good, and I took a part-time job at a grocery store to help make some money. Sometimes I worked late, so I had irregular hours.

Living with Chris was getting comfortable, and I started relaxing around him. Occasionally I would walk around the house in the morning in just my boxers and a-shirt. I would catch Chris checking me out, and he would quickly look away. He wasn't really my type, but I enjoyed the attention and was a little lonely without Mark in my life.

I started showing off a little more in front of Chris. Sometimes just wearing boxers and no shirt. I was having fun catching Chris glancing at me.

One night around 10 while studying on the couch, Chris came out of his room with a full laundry basket.

"I'm going to the laundromat. See you later."

"It's pretty late. Do you want a ride?"

"No thanks, I can walk. It's not too far."

"Otherwise I was going to do some laundry tomorrow. I can drive us then."

"No, I'm busy the next few days, and I gotta get it done tonight. I'm all out of underwear", he laughed.

"Hell, I'll lend you some underwear for a few days."

"Ummm, no thanks. I can get it done tonight."

"Hey, it's not weird for me, if it's not weird for you. Just don't leave any skid marks in them."

"Well, I don't know..."

"I'll get you some and then you won't have to go tonight."

I went into my room and found three pairs of boxers for Chris, in light blue, yellow, and white with triangles and circles.

"Here you go. You need any t-shirts or anything?"

"Thanks. No, I have enough shirts. I've never worn boxers before."

"I just started wearing them last year, and I like 'em a lot."

"Yeah, I see you wear them around here."

"Well, good. Then I can see you wear them around here too. Go ahead, try them on. Let me know how you like them."

Chris went into his room and came out a few minutes later, still fully dressed.

"Yeah, they fit great. Thanks."

"Hey, I thought you were going to model them for me? Come on, you've seen me in them."

"Right here?"

"Yeah. Take off your jeans and walk around for me."

Chris quickly followed my suggestion and took off his jeans, showing the light blue boxers.

"Anything else?"

"Yeah, take off your shirt and t-shirt too."

"Ok."

Chris stripped out of his shirt and t-shirt and stood in front of me in just his boxers. He seemed to like being ordered around.

"Turn around for me."

Chris obeyed and turned in a circle.

"Very nice. Those boxers look good on you."

"Not as good as you look in yours," Chris replied quietly.

"Do you like seeing me in my underwear?"

Chris looked down and nodded. "Yes."

"Would you like to see me in my underwear now?"

"Yes, please."

I was enjoying this immensely.

I stood up and slowly took off my shirt and a-shirt. Then I slowly undid my belt and opened my jeans, letting them drop to the floor. I stood in front of Chris, wearing just my white boxers with red and blue paisley designs on them.

"There. How do I look?"

"You look very sexy. Any girl would be lucky to be with you."

I glanced at Chris and saw a boner beginning to tent the front of his shorts.

"What about any boy?" I grinned.

"Do you like boys?"

"I like boys and girls," I told Chris. "What about you?"

"I've never been with either, but I think I like boys. I like what I see right now." He smiled.

I kicked off my jeans and walked over closer to Chris. He looked up and met my eyes.

"Would you like a hug?" I asked.

"Oh, yes," he exclaimed. We hugged each other, bare chests touching. As we squeezed, I could feel our cocks get hard in our shorts and rub against each other.

"Let's go sit in the couch," I suggested.

We sat next to each other, our legs lightly toughing.

"Another nice thing about boxer shorts is the easy-access front..."

I reached over and brushed my hand against the tent in Chris' shorts. He let out a soft moan as I lightly stroked my hand across his hard rod. It started twitching, and soon the pink head popped out of the fly and stood at attention.

I slid my fingers around his cock and tugged gently. Chris started groaning. I began slowly jacking his cock, and he leaned back on the couch, mouth open and making little pleasurable noises.

I moved my other hand along his thigh and up the leg opening of his boxers until I felt his soft pubes and gently caressed his balls.

Suddenly Chris cried out and a huge load of cum erupted and shot all over his chest and my hand. He must have been saving up, because it spurted over and over big thick gobs of white cream.

Chris quickly sat up. "I'm so sorry! I got jizz all over your shorts!"

I laughed. "It's not like it's the first time that happened."

He smiled back. "Ok, good. Oh god, that felt so good! I was getting so horny seeing you walking around in your underwear. I never thought we would do this!"

"It's our little secret," I whispered. Then I leaned over and kissed him, tasting a few drops of cum that landed on his lips.

"Can I touch you now? I am so horny for you."

"By my guest," I told Chris as I leaned back on the couch.

He got on the floor in front of me, and started playing with the big tent in my shorts. He kissed my cock through the material, and rubbed his hands along the length. In no time, my cock poked his head through the fly opening, and Chris bent in to lick the round top.

I thought back to Mark sucking on my dick, and instantly got rock hard, as Chris took me in his mouth and began bobbing up and down. I stroked his hair as he sucked faster and faster.

"I'm going to cum soon if you keep that up. You may want to pull out."

Chris sat up and looked at me. "I want to taste your cum and suck you dry." Then he went back to working on my cock.

Wow, this skinny little guy was really good. In just a few more minutes, I warned him I was about to cum, and he kept it up until I exploded in his mouth. I heard him gag as he gulped down my huge load. He softly licked my cock clean.

"At least I kept your boxers clean," he told me.

"Come here!" I called, and pulled him to me, as we lay on the couch with Chris on top of me. I could feel his sticky chest and shorts rubbing against me, and it made us feel more intimate.

"Wasn't that more fun than doing laundry? Let's go take a shower, and you can sleep with me tonight."

***

We woke up naked in my bed the next morning and had a quick morning wood mutual jerk-off before getting up for school.

"Well, that's more laundry to do now," I laughed as I looked at the cum stains on my sheets.

Chris left for school and I gathered up my laundry. I only had two morning classes and was going to head right to the laundromat after that. I thought I would be a nice guy and take Chris' laundry too. I went into his room and got the basket I saw him holding last night. I took both baskets with me to my car and left for school.

After my last class, I arrived at the lanudromat and began sorting our clothes. I set up a load of jeans and dark clothes, then began setting up one for sheets and underwear. I noticed that Chris had a lot of tighty whities, and they were pretty ratty - frayed and dingy and threadbare in places. We were definitely going to have to upgrade his underwear.

At the bottom of the basket, I noticed two pair of ladies nylon panties - purple and pink. That was weird, Chris told me he liked boys. I examined them and saw stains in the crotch that smelled like cum. He must jerk off in them. Oh well, I threw them in the washer along with the other underwear and started the loads.

I did my schoolwork while the laundry was washing, then loaded the clean wet clothes into the dryers. It was kind of fun examining and folding another guys clothes, especially the underwear and surprising panties. They smelled so fresh now.

I went back to our apartment and when Chris got home he saw the basket of his clean clothes on the floor.

"Hey! Did you do my laundry! I told you I was going to do them in a few days!" He seemed embarassed.

"No problem. I went to do mine, and thought I would do yours too. No big deal."

"Well, I wasn't ready for that!"

"Whoa, I said, not a big deal. We were pretty close last night, I don't think washing your clothes crosses any line."

"I'm sorry. I guess I'm embarassed with what you saw."

"What? The panties? I was curious, but it's not my business", I grinned.

"It's always been my secret. Once in a while, when I feel pretty, I like to wear women's underwear. It makes me feel special."

"That's cool. I bet you would look really sexy in them. Maybe you could show me some time? I'm sure they would look better than your old tighty whities. Man, we have got to get you some new underwear! Those old ones are falling apart!"

"You're right", he laughed. "I just feel weird buying underwear. I've had those briefs for years, and I stole the panties from my sister."

"You have time now? Let's go buy you some underwear!"

I drove us to the other side of town where they had a K-mart. We walked through the men's department and came to the racks of underwear. I found some full-cut boxer shorts I liked, a package of three in white with red geometric designs with snaps in front.

"Chris, do you like these? They would look good on you."

"Hmmm, I'm not sure I'm ready to cut over to boxers yet. Can I share yours once in a while?" he smiled.

"Sure, just remember, no skid marks! I'm going to buy these for me then."

Chris walked over and picked up a 3-pack of bright white briefs with thin black and red stripes on the waistband.

"Do you like these?" he grinned.

"Anything is better than those old grey ones! You would look really sexy in those."

"OK, I'll get two packs. If I need more than that, maybe I'll borrow some of your boxers?"

"Sure, help yourself to my underwear drawer", I told him. I leaned closer to Chris and whispered, "Do you want to get some new panties too?"

"Oh, man, no!" he blurted out, then quieted down. "There is no way I could buy ladies underwear!" he whispered.

"Relax, I'll buy them for you. You pick out what you like and I'll get them with my stuff."

"Really? Are you sure? You wouldn't think that's too weird?"

"No problem. It's nobody's business. Pick out what you want."

We walked over to the ladies department, making sure no one was watching us. Chris looked over the rack of underwear packages.

"How about these?" He held up a 3-pack of nylon panties, in white, light blue, and yellow pastels.

I grinned. "You would look really hot in them!" I whispered.

Chris tossed them to me and said, "OK, let's get out of here!"

We picked up a few other miscellaneous items and went through the checkout. Chris went first with no problems. The bored cashier raised her eyebrows when I checked out with boxer shorts and panties, but didn't comment. She must see a lot of weird things.

As we drove home, Chris opened the bag and took out the underwear. He was like a kid in a candy store, as he opened each package and held up the underwear to examine it.

"This was so fun. I can't wait to model these for you!"

We got to the apartment, and Chris started stripping in the kitchen. Man, for a guy who was so shy a few days ago, he sure didn't mind undressing now.

He put on a pair of the bright new briefs and turned around for me to see. I gently caressed his butt and told him how sexy he looked.

"Come on to bed - I want to thank you for today!" Chris started undressing me as he led me to my bedroom. He stripped me down to my white boxer shorts and we climbed between the sheets.

Chris was like a new person, confident and gentle, as we kissed and caressed each other. It seemed like forever as we rubbed our bodies together, kissing and running our hands all over each other. I could feel his warm bare chest against mine, as well as the hard cock in his briefs rubbing against mine in my shorts.

We kissed slowly, tasting each others lips and tongues. He was easily the best kisser I have ever encountered, male or female.

"I feel so open with you. You don't judge me", Chris whispered to me. "I want to make you feel so good."

Chris slipped a hand inside my waistband and softly stroked my hard cock. I almost came right there. "Can I suck your cock?"

"Please do", I whispered back.

Chris moved down the bed and pulled my boxers down. My cock sprang to attention as he slid the shorts off each leg. Then he spread my legs and moved down to kiss my balls.

I moaned in delight as he lightly sucked on my balls, then stroked my cock. He moved his mouth to my throbbing head and licked it, getting his warm saliva all around. He slowly took my cock in his mouth, sliding it in and out as he softly caressed my balls.

He took me to the edge and back over and over until I couldn't take it any more. "I'm going to cum!"

Chris grabbed my cock and squeezed it as he jacked me off in his mouth. The hot semen spurted out of me in a jet, gagging Chris, as he tried to contain it all.

"Aaaaaaaaaah! Fuck! That feels so good!" I moaned.

Chris gently licked my cock clean until it became soft, then he climbed up in my arms and we kissed some more.

I reached down to pull off Chris' new briefs and he said, 'No, leave them on please. They feel so good I want to cum in them."

That got me hard again, so I laid Chris on his back, and gently rubbed his cock through the material, feeling it get warmer and harder as I went. He squirmed a bit and let out some soft groans, as I sped up the rubbing.

Suddenly he blurted out, "I'm coming! Don't stop!" I kept massaging his cock and felt it jerk and erupt inside his briefs. I felt cotton fabric get sticky and saw the wet stain spreading as more and more cum oozed out. I kept massaging until his cock got soft again, then I moved up to kiss him again.

We lay like that for some time, softly talking and holding each other. Chris basically moved into my room that night, sleeping together with me from then on.

We consolidated our underwear drawers into one and shared our different styles, and explored each others fantasies in depth.

And yes, he did look really sexy in the ladies panties....