Adventures in Boxer Shorts

When I was in college, I started dating this girl, Lisa. We had made out a few times, but nothing beyond that...yet.

One spring Sunday, she called and asked if I wanted to go for a bike ride. Her sister Julie and Julie's boyfriend, Tom, were in Europe for two weeks, and Tom had asked Lisa if she would stop by his house and water his plants while he was gone.

I rode to Lisa's apartment, then we rode to Tom's house halfway across town. We had a nice time chatting as we rode, while the sky quickly turned cloudy and windy, preparing for an unexpected spring storm. About a mile from Tom's place, it started to rain. We pedaled faster, but it began to rain harder, and by the time we arrived at his back door, we were soaked.

Lisa unlocked the door, and we hurried inside, dripping all over the hall rugs. Lisa told me to wait there and she would find some towels. She ducked into the bathroom and came out a few minutes later, with a towel wrapped around her head, and another around her body, like she had stepped out of the shower.

"I threw my wet clothes in the dryer", she told me. "There is a towel on the counter if you want to do the same. I'll see if I can find us something else to wear."

She went down the hall as I entered the bathroom. It had a washer and dryer, and the dryer door was open. Inside were Lisa's clothes -- shorts, t-shirt, and matching baby blue bra and panties. I smiled as I imagined her lean athletic body in her underwear.

I stripped out of my soaking wet t-shirt and shorts, emptying my pockets, and throwing the clothes in the dryer. I looked like a drowned rat in the mirror, my white briefs soaked and sagging, almost see-through. I took off my briefs, wrung out the water in the sink, and threw them in the dryer.

I was drying off with the big bath towel when Lisa knocked on the door and opened it slightly, her arm reaching in and setting a small pile of clothes on the counter.

"I found some of Tom's clothes for us, while our stuff is drying."

I had been hoping we would sit around naked, but now I imagined her wearing baggy sweat pants and a loose t-shirt.

The door shut again, and I walked over to the new clothes. It was only a white athletic-shirt and a pair of white boxer shorts with little red and blue triangles on them.

I only owned white briefs, and had never really considered boxer shorts. They seemed too old-fashioned, although some of the guys in the gym were starting to wear them. It seemed weird to wear another guys underwear, but they looked relatively new, and were freshly washed, so I thought, what the hell.

As I slid on the boxers, I thought they felt great. Kind of like slipping into bed naked and the sheets were just washed. I liked how my cock and balls hung free, and they didn't look too bad in the mirror either. I slipped on the tight-fitting A-shirt, and thought that felt and looked pretty good too.

Opening the door, I saw Lisa in the hall, but instead of sweats and a t-shirt, she was wearing a matching white A-shirt and a pair of Tom's white briefs. I had never imagined a woman wearing men's briefs, but she looked really hot in them. The A-shirt hugged her body tight, her firm breasts straining at the material. I could see her hard nipples poking up through the fabric.

"Wow! You look great!", I told her. "You should dress like that more often."

Lisa laughed. "You look pretty hot yourself. And maybe a little excited to see me." She was glancing down at the tent forming in my boxers.

"Uh, yeah", I smiled embarrassed, as I adjusted myself a little.

Lisa shut the dryer door and started drying our wet clothes.

"Why don't you see if there are any weather warnings on TV? I'll see if Tom has any beer in his fridge."

There were no storm warnings on the local channels. It looked like the storm would blow over soon. I sat on the couch, and Lisa brought in a couple bottles of beer.

"I like your taste in clothes," I told her.

"I always wanted to try on tighty-whiteys," she smiled. "They look so snug and soft. And when I saw the boxer shorts in Tom's underwear drawer, I knew I had to see you model them for me."

"I really like them. I've never worn them before, but could see myself getting used to them. But I really like that look on you."

Lisa sat down next to me, and I put my arm around her. We started kissing, both more than a little aroused by the state of dress and opportunity for privacy. Our tongues lightly touched, as our kisses warmed up. Sliding my hand on her side, I caressed the edges of her firm breast through the soft material. I brushed against her erect nipple, and she let out a low happy growl.

I felt Lisa's hand slide down my back, around my waist and across my hard cock. She stroked it through the boxers, then slid her hand inside the fly and ran her fingers along the shaft. I squirmed and kissed her harder. Her hand grabbed around my throbbing member and pulled it out the open fly.

"Mmmm, what do we have here?" Lisa asked me, as she gently stroked my cock. The boxers were loose enough that my cock could easily poke out and not get caught up in the material, like my briefs.

She slowly slid off the couch to kneel at my feet, still stroking my hard rod. She lightly kissed the tip, sending shivers up and down my spine. Lisa took my cock in her mouth, licking with her tongue, and sucking on the shaft. I could feel the warm wetness as she slid my cock in and out of her mouth.

It was the weirdest experience. I was sitting in a strange house, on some guy's couch, wearing his underwear, and getting the blowjob of my life. Didn't expect that when I got up that day.

Lisa kept it up, speeding up and slowing down, licking, sucking, kissing. She opened the fly in the boxers wider, then gently pulled out my balls as well. She took each one in her mouth, kissing and lightly sucking on them. Then she massaged my balls as she returned to sucking me off.

"You better pull out soon, cause I can't hold it much longer. This feels so good!"

She looked up at me, smiling, and said "I want to taste your seed and suck you dry. Let it go!" My cock was back in her mouth, and picking up speed.

A few more minutes, and I groaned, "I'm cumming...", and shot a huge load, as she gulped and slowly milked every drop from my throbbing cock. She licked me clean, as my cock relaxed. Then she gently tucked me back in the boxers and crawled up on the couch.

We kissed, and I could faintly taste my cum in her mouth, as she rubbed her chest against mine. We were both so horny.

I spun her around on the couch, laying her back, as I caressed her breasts. I kissed her neck and worked my way down to her hard nipples, taking each into my mouth. She arched her back as I nipped on her sensitive points. Sliding my hand inside her A-shirt, I stroked her breasts, then pulled her shirt up to expose her bare chest.

As I stroked her chest and body, I reached down to caress her pussy. The briefs were very wet between her legs, as my fingers massaged the tender area. I spread open the fly opening in the briefs and slid a finger inside, coming into contact with her sticky pussy. I gently ran my finger between her swollen lips.

"Mmmm, somebody is very wet here..."

"Oh god, that feels so good!"

I slid off the couch so my head was in front of her pussy. With a finger, I gently pulled one leg opening back and licked the side of her pussy. It tasted so warm and salty. She moaned in delight.

It seemed a little weird to me, having my face so close to men's briefs. I reached up to the waistband and began pulling them down, almost expecting a big dick to pop out. But what I saw was a neatly trimmed pussy, glistening with juices, and red lips spread open. Her clit was red and erect, begging for me to suck on it.

I licked her moist labia lips, gently sucking on the outer ones, and running my tongue around. I kissed her pussy like it was an open mouth, and tasted her strong musky juices. My tongue darted into her warm pussy as she arched her back and moaned in delight. I ran my tongue around her clit in little circles, alternating with gently taking her erect button between my lips and sucking on it.

I took my time, speeding up and slowing down, as her legs started trembling. She was so wet as her juices continued to flow into my mouth. My cock was stirring again, getting hard and poking its way out of the fly in the boxer shorts. She grabbed my head and pulled it tighter to her pussy.

"Oh yes! Eat me! You're driving me crazy!"

When she finally couldn't take any more, she cried out "I need your cock in my pussy! Hurry!"

I wasn't expecting any sex when I went on our bike ride today. "Does Tom have any condoms? I don't have any with me."

"It's okay, I'm on the pill. Just slide your big boy inside!"

I started getting up so I could slip off the boxers, but Lisa reached out grabbing my cock protruding from the boxer fly, and pulled it toward her soaking wet pussy.

"Fuck me!"

My cock slid easily between her moist lips. She gasped as I slid all the way inside. I'd never fucked anyone while wearing underwear before, but the boxers had a big enough fly that I could protrude comfortably. Lisa grabbed my ass and pulled me in tighter. Her legs wrapped around me as she writhed in ecstasy.

"Fuck me! I want to feel your cum!"

Before I knew it, Lisa stiffened up and let out a yell, "Oh god! Yes...yes...YES!" She climaxed and squeezed me tight. Suddenly. I found myself cumming again, shooting another big hot load into her wet pussy.

We slowed down, enjoying the tingle, when Lisa burst out, "Quick, sit me up! I'm leaking on the couch!"

I grabbed her under the arms and sat up, pulling her to straddle my lap, all without my cock leaving her pussy. We laughed and hugged, as I felt our combined juices running into my lap.

Soon, my cock relaxed and I felt it plop out of her pussy. Lisa reached down to the floor and picked up the briefs, holding them to her crotch, and climbing off my lap. She tried to wipe up some of the juices as I looked down at my crotch. The boxers were soaked through, almost transparent, with our cum - thick ropes of sperm across the wet material.

Lisa laughed and said, "It looks like we'll be doing a little laundry to cover our tracks. Luckily there is only a small wet spot on the couch."

We walked to the bathroom and she threw her wet briefs and A-shirt in the washer. I added my A-shirt and soaked boxers. She started the load, while I checked the dryer for our clothes. They were still a little wet, so I gave them another few minutes of the drying.

"I can't believe how wet I was!", Lisa exclaimed.

I picked her up and set her on the bathroom counter. "Let me clean you up."

I knelt down in front of her, spread her legs, and began licking out her wet pussy. I was tasting both of our cum, sweet and salty and warm. Lisa leaned back and enjoyed the attention, purring like a cat.

In no time, she was squirming and spreading her legs wider, pulling my head in closer. She came again, and I continued licking up her juices. Finally she pushed me away.

"Let's take a quick shower. I need to cool down."

We climbed into the shower stall and had a sensuous washing, cleaning all of our sticky parts. We dried off and threw the wet towels back in the dryer, our original clothes now dry. The washer finished its small load, and we added Tom's underwear.

As we dressed, I handed Lisa my white briefs. "You can wear these home," I offered. "Something to remember today by."

She laughed and accepted my offer, sliding on my briefs. "Do you want to wear my panties?"

"Hmmm, I think I'll go commando, but I'll take your panties home and can trade them with you when I see you next."

We finally watered Tom's plants, then cleaned up the beer bottles and checked the couch -- no permanent stain. The dryer beeped, and we took out the clothes and towels, folded them and put them away.

I followed Lisa to Tom's bedroom, where she put the A-shirts and underwear back in his dresser drawer. Tom had several pairs of boxers, white, pastel colors, stripes and patterns, and several pairs of white briefs. Whenever I saw Tom next, I was going to wonder what he was wearing underneath.

The rain had let up, and the sun came out, so we rode our bikes back home.

The next day when I got home from classes, my roommate, Phil, was leaving and told me, "Some girl stopped by and left you a package. I put it on your desk. See you later."

I found it and opened it up. It was a 3-pack of athletic shirts, and two 3-packs of boxer shorts. One pack was solid pastel colors -- blue, green, yellow. The other three white with red pinstripes, little boxes, and little diamonds.

The note said, "Had a great time yesterday. Think of me when you wear these. Maybe you can model them next time I see you. And if you don't know what to do with any of your old briefs, you know who you can give them to. -L "

And I did.