8 comments/ 74685 views/ 9 favorites Underwear Friends By: ramon25 I was dreading taking a gym class in my senior year in high school. I missed gym in my junior year due to some surgery, so I had to take it as a senior in order to graduate. All of the other guys were juniors that i didn't know very well, but I had to make the best of it. Partway into the school year, a new guy transferred to our school from Texas. Mark was eighteen like me, and a senior, and needed to take a gym class to graduate as well. We became friends and hung out together. Being from so far away, Mark was pretty different than the rest of us Minnesotans. The accent and phrases were obvious, but in the locker room he was the only guy to wear A-shirts and boxer shorts. The rest of us wore standard tighty whitey briefs and t-shirts of various colors under our clothes. But Mark always wore white A-shirts and white boxers with some kind of little pattern. One day while getting dressed, he was wearing a pair of white boxers with little red and blue shields on them. I finally commented, "Those are some cool boxers. No one else around here wears them." "Thanks. At my old school, that's what every guy wore. I like how roomy they are. I don't think I could ever go back to briefs." I think he liked the attention I was giving to his shorts, because I noticed a little tent forming as he pulled on his jeans. I thought about his boxers a lot, and checked them out each day in the locker room. I wondered how they would feel. One day as Mark was dressing, he accidentally dropped a pair of boxers on the floor near my feet. I picked them up, and quickly inspected the green diamond pattern as I handed them to him. The material felt cool and crisp - I bet it would feel good against a cock and balls. "You should get some boxers, man. I think you'd like them." "My mom always buys us white briefs every Christmas. It would be weird to talk to her about buying me boxer shorts instead." "You should come over some time. I'll let you borrow a pair of mine to see if you like them." "Thanks, man. Maybe I'll do that." I was both excited and a little scared to think about that. I was a little unsure about my sexuality, but that might be taking a big step to wear another guys underwear. Yet, those boxers where very intriguing... I didn't bring it up the next day, but I could tell Mark was still thinking about it. "Hey, Ray. You're pretty good in math. I'm having some problems in my class. Would you help me a little with my algebra assignment?" "Sure. When do you have some time? Do you have a study hall?" "No. But you could come over after school tonight. It's just me and my mom, and she works until six every night." Was that an invitation? Or just a simple study request? "Sure. I'll meet you by the front doors after school." The rest of the day, I was thinking this might be a chance to try on a pair of boxer shorts. But I didn't know how to bring it up without sounding queer. I met Mark by the door and we walked home to his house. "I really appreciate the help, Ray. How can I repay you? Can trade you a pair of boxers for your time?" "You don't have to pay me. I'm glad to help. Besides, if my mom found a new pair of underwear in our laundry, I would have some explaining to do." "Well, you can at least try on a pair while you're over. You can decide if you like them, then ask your mom to buy you some for Christmas instead." "Yeah, that's a good idea." We got to Mark's house, which was empty like he said. I called my mom and told her where I was. He got out his algebra book on the kitchen table, then got us each a glass of soda. Then he went into his bedroom and came back with an A-shirt and pair of white boxers with little blue and red patterns. "Here, Ray. You can try these on while we work and see if you like them. I brought you an A-shirt to try too." "I don't want to sit here in just underwear in front of you." "Why not? We are in underwear every day in the locker room. Here, I'll strip to my underwear now too. Mark took off his shirt and pants. He had on his usual A-shirt and a pair of white boxers with thin blue stripes. "Ok, I guess." I took the clothes he offered and asked, "Where is your bathroom to change?" Mark laughed. "Ray, you change in front of me every day. It's not like I haven't seen you naked before." I laughed too. "Sorry, you're right. I just didn't want to seem to weird to you." I took off my shirt and pants, but modestly turned my back to Mark as I removed my briefs and t-shirt and pulled on his underwear. The crisp material felt great against my cock, which had plenty of room to start getting hard. I turned around and modeled them for Mark. "They fit great. How do they look on me?" "Wow, Ray. You look very cool. You should wear underwear like that all the time." "I'll wear them for a while and see how I like them. Let's start on your homework." I sat at the table, and Mark sat next to me. For the next half hour, we went over his assignment, and I tried to explain how to solve the problems. From time to time, I would catch Mark sneaking a look at my crotch, which only made me a little more excited. A few times, I had to adjust my cock in the shorts, so it wouldn't try to pop out the fly. We finished the work, and still had about two hours until his mom came home. "Well, how do you like the boxers and A-shirt?" "I think I like them a lot. Now I'll have to figure out how to talk to my mom about getting me some for Christmas." "What kind do you like? White, solid colors, patterns?" I hadn't thought of that. I had just seen Mark's, which ran to white with patterns or stripes. "Come on, I'll show you different kinds that I have." I followed Mark to his upstairs room, and he opened his underwear drawer for me. I looked inside, and saw several solid colored ones in light blue, yellow, peach and white. But most of them were small patterns on white - boxes, diamonds, shields, dots or 'x's. I picked up a few pairs to look at them closer. Mark really liked my attention, and came closer behind me, and gently placed a hand on my ass. I jumped, but really enjoyed the touch. He rubbbed my ass a little, and I turned around to look at him. He was so close to me, that our erect tents in our shorts touched. He laughed, and put his hands on my hips. "I really like you, Ray. It feels really special how close we've become." I was scared and aroused at the same time, but I really wanted to touch and kiss him. I put my hands on his hips' "Me too, Mark. I've never felt this close to another guy before." We stared into each others eyes, and Mark leaned forward to kiss me. His lips felt so warm and tender on mine. I kissed him back and hugged him close, our cocks touching through the fabric. We kissed for a while, out tongues exploring, when Mark whispered in my ear, "Have you ever touched another cock before?" I quietly replied, "No." "Would you like to touch mine?" I couldn't help myself. "Yes" Mark reached down and pulled his hard cock through the fly in his boxers. I reached down with my hand and lightly grabbed it. It felt so warm and hard in my hand. I gently slid my hand up and down the shaft as Mark softly moaned. "Oh man, that feels so good." I wanted to please him so badly. I kept lightly stroking his cock, feeling him squirm. "Not so fast there, Ray. I don't want to cum in yout hand. Can I touch your cock too?" I was hoping he would ask. "Yes, please." Mark spread open my fly and pulled out my throbbing cock. He deftly began stroking it. "Oh God, that feels so good!" "Do you know what feels even better? Can I put your cock in my mouth? I'll be gentle." I was scared, but a lot more excited. I had gone this far, why not? "Oh, yes. Please suck my cock." Mark kneeled down in front of me, and pulled down my boxers, careful of my hard cock. I stepped out of the shorts, and he kissed the tip of my throbbing cock. I felt him lick the shaft, and I looked down to see him take the cock in his mouth. He slid my cock in and out of his mouth, the pleasure building. Mark helped me back to the bed to sit on the edge, and he kneeled in front me again. As he sucked on my cock, he cupped my balls in his hand and gently massaged them. After a while, he kissed my balls, and took them in his mouth one at a time, gently sucking on them. He moved back to sucking on my cock, and I couldn't hold it much longer. "I'm gonna shoot man!", I cried out. Mark sped up, and I felt a huge load of cum erupt and spray in his mouth. He gagged a little, but kept swallowing. Then he sucked clean my cock and kissed the head, before moving up to kiss me on the mouth. I could taste cum on his lips, but I was so excited, I licked his lips for more. That was my first blowjob, and from a guy yet, but it was incredible! I reached down to caress Mark's stiff cock, sticking through the fly in his boxers. "Can I suck your cock now?" "Oh yeah, man!" He stood up, and I kneeled at his feet, removing his boxers and taking his thick cock in my mouth. I had never done this, but i tried to remember some of the things Mark did to me. I was eager to please him. As I sucked his cock, he placed his hands on my head, and guided me in and out around his cock. "Play with my balls, too, Ray. I really like that." I cupped his balls and gently massaged them. He squirmed in my hands. "Do you want me to cum in your mouth?" I grunted , "Uh-huh." "Let's go to the bed." He helped me lie on my back, and straddled my mouth with his balls. I alternating sucking on each, as he groaned in delight. "I want to fuck your mouth now." I propped myself against the headboard, as Mark straddled my chest and placed his thick cock in my mouth. He thrust in and out of my mouth, as I caressed his bare ass cheeks. "I'm cumming, man!" Mark shuddered, and tensed as a thick stream of cum shot into my throat. I gagged, and felt some run down my chin. It was warm and salty, and I swallowed as much as I could. I cleaned his cock off, licking and sucking the strings of cum. Then he lay next to me and we kissed, letting him taste his own cum. We made out like that for some time, before Mark said, "My mom will be coming home soon. Let's clean up." I gave Mark his underwear back, and we got dressed. "Let's do that again!", we both blurted out, then laughed. "That was so hot wearing your boxers and A-shirt. I gotta get some of my own" "You can always come over here and wear mine until you do." "I think I will!" Underwear Friends Ch. 02 I couldn't stop thinking about my encounter with Mark. I was pretty sure I still liked girls, but I was so hot for Mark! I longed to kiss him, undress him, stroke his cock and slide it in my mouth again. And have him do the same for me. I got to see him four days a week in gym class, and loved watching him strip to his boxers and A-shirts. The rest of the guys in class, including me, wore tighty-whitey briefs and colored t-shirts, but Mark transferred here from Dallas, and all the guys there wore white boxers with little patterns and white A-shirts. During our encounter last week, Mark let me try on his underwear, and I liked them so much, I was determined to switch myself. Every year for Christmas, along with our other presents, my mom would always buy my little brother and me new underwear, white briefs from JCPenney. My dad always got a pack of boxer shorts, but I never really thought about them before. I never saw him in his underwear, and besides, men wore boxers, boys wore briefs. However, now that I was eighteen and a senior, I could start dressing more like a man. My mom was fixing dinner, and I was setting the table. "Mom, are you planning on getting us underwear for Christmas again?" "Huh? I guess I was thinking of that again. Why, do you want something special?" "Yeah. I was thinking of trying boxer shorts and A-shirts. Some of the guys in gym class are switching to them. They seem more for older guys." My mom laughed. "Well, I guess I didn't think of that before, but sure, I suppose I could pick some up for you. Do you want to pick them out with me?" Be seen shopping for underwear with my mom? "No, that's okay, surprise me. The guys are wearing white boxers with little patterns. I'm not sure where their moms get them from. You can probably try Penney's. I'd also like to try some A-shirts if you can find some." "I'll see what I can do." "Thanks, Mom." I started imagining what kinds of shorts she would get. Mark had shown me his underwear drawer, and he had a lot of variety. The next day at school, Mark asked me if I wanted to help him with his algebra again. He winked at me and smiled, and I flashed a big smile back. "I'd love to." As we walked to his house after school, I told him how I asked my mom to get me some boxers too. "Cool, man! You looked so good wearing my boxers. I can't wait to see you wearing some new ones. I hope I don't get a hard-on watching you undress in the locker room." "Now you know what I have to avoid when I see you undress!" We got to his house, and as usual, his mom was working. We had about three hours. "You want to wear my underwear while we work again?" "You bet! Pick me out something hot, and I'll call my mom to let her know I'll be late." I set out our math books, and Mark came back with a pair of white boxers with little blue diamonds and an A-shirt for me. I undressed and slipped on the clothes he gave me, while Mark striped down to his yellow boxers and A-shirt. We checked each other out and smiled. Mark kissed me, and we sat down to do homework. Mark kept sliding his hand to the tent in my shorts, and I pushed him away. "Man, we'll never get this done if we start that now. Tell you what - you finish your assignment and I'll check it over. If you get 80% right, I'll give you a 'B' for 'blowjob'. How's that?" Mark laughed, "Wow, that's incentive! If I had that offer before, I'd be a math genius by now!" We worked on our homework. I helped Mark out with a few questions, and soon he was done. I checked over his work - 13 right out of 15 - 87%. "You pass! Now, let's give you your reward." Mark slid his chair back from the table, and I kneeled down in front of him. I opened the fly in his yellow boxers and pulled his hard cock out. "Mmmm, somebody looks good enough to eat!" I gently kissed his soft cockhead and ran my tongue around the rim. Mark moaned in delight. I slid my hand around the shaft, and slid his cock in my mouth. I lightly sucked on his throbbing member, as I jacked it in and out of my mouth. I wanted to please him so badly, and I loved hearing his little moans of delight. It was so sexy sucking him off in his shorts, and before he knew he, he yelled 'I'm cumming!", and he shot his load in my mouth. I gulped as I tried to contain the cum explosion. He was so warm and salty. I licked off thick strings of his wad from his cock, smacking my lips as I swallowed them. His cock clean and getting limp, I moved up to sit on his lap and kiss Mark's soft lips. He slid his tongue in my mouth, eager to taste some of his cum on my lips. We kissed for some time, exploring each other's mouths, until my throbbing cock was poking him in the belly, and he laughed, "Your turn". We switched places, me sitting on his kitchen chair, and Mark kneeling at my feet. He pulled my hard cock out of the fly of the boxers, and slid the whole length down his throat. Mark bobbed his head back and forth, my cock sliding all the way in and out of his mouth. I placed my hands on his head, and gently caressed his hair as I guided him. I was so aroused, sitting there in Mark's boxers with the little blue diamonds, as I watched my cock disappear in his warm mouth. In no time, I felt my balls quivering, and I shot a huge load in his mouth, Mark gagging as he swallowed my seed. I saw some dribble out of his mouth. Mark pulled away, and I guided his face to mine, licking my cum off his chin and kissing those sticky lips. He sat on my lap, and we made out as before, kissing and caressing. We stood up to get dressed before Mark's mom got home. I handed him back his underwear and put on my briefs. "Man, I never knew underwear could get me so horny! My dad wears boxers and I never thought they were sexy until I met you." "Your dad wears boxers? Cool! What kind?" "I guess mostly white, I really don't know. Once in a while I see them in the laundry hamper." "I think men's big boxers are so hot!" "I'll see if I can sneak a pair of them over here to show you." "Oh man, that would be great!" Mark and I both had part-time jobs, so we only had one night a week where we were both off. We decided to make it a regular 'tutoring' session. The next week, I snuck into my parent's room, and checked out my dad's underwear drawer. As I thought, he had mostly white boxers, but I also saw a pair of light blue ones and a white pair with hearts on them. I didn't think he would miss a pair of the white ones, so I grabbed one from the bottom of the pile and slipped it in my backpack. I would show them to Mark after school that day. As we walked to Mark's house, I told him I brought him a surprise. "Your dad's boxers? Wow, I can't wait to see them!" We unloaded our stuff on the table, and Mark said, "I don't have any homework tonight. Can I see your dad's shorts now?" I laughed, "Easy, big fella!" I reached into the bottom of my backpack and pulled our a bag. I took out the shorts, they were large full-cut white boxers with snaps in the front. They looked a few sizes bigger than what Mark wore. "Can I try them on?" "Sure, model them for me." Mark stripped down right there, and slipped on my dad's boxers. They hung very loose on him, and he instantly got an erection that made a tent. "I feel like an real man in these. Wanna play a game? You can be my son." "Sure, okay." "Let's go to my room." Mark sat in his bed, his cock poking a tent in the big white boxers. "Ray, get in here! The school just called, and you're failing English! They said you've been skipping class! I'm very disappointed with you. You need to be punished!" I laughed, "Man, this game doesn't look very fun to me. Who wants to fail English?" "Just play along, it will be fun." "Okay." "Get over here and take off your jeans. You're going to get a spanking!" I thought it was a little weird, but what the hell. "Yes, sir." I took off my shirt and jeans and walked over in just my little white briefs. "Lay across my lap. You need to learn a lesson, son." I laid across Mark's lap, and he began spanking my ass. "Ouch!" I tried to get up, but Mark was firm with me, and kept up the spanking. As we struggled, I noticed I was getting very hard. This was kind of kinky, but horny. Mark grabbed the waistband of my briefs and pulled then down, baring my ass. "You need to learn a lesson that I am the boss, and you will obey me!" He started spanking my bare ass, but I liked that too. Here we were, two guys the same age, but with his big boxers and my little briefs, we easily slipped into a father/son roleplay. And we both found it very arousing. "I'm sorry, sir! I won't do it again. I'll do whatever I can to please you!" "I'm very angry with you, son! It's going to take a lot for you to please me." "Okay, I'll work hard. I know what you would like. Can I suck your big cock?" "Yes, that would be a good start." I got off Mark's lap and kneeled in front of him. I opened the snaps of his boxers and pulled back the material, and his hard cock spilled out. "I'm sorry sir, let me please you." I took his cock in my mouth and started eagerly sucking on it. His shorts were so loose, I slipped a hand up the leg opening and massaged his balls. I was getting rock hard - this was a very exciting roleplay. "That feels very good, son. But I think tonight we need to go further. You need to let me fuck you in the ass." "What?" Mark slipped out of the roleplay. "Only if you want to, man. I'll be gentle. I am so hot for you right now. What do you say?" I thought it over, and agreed to let him try. Neither of us had done that before, but we were so hot for each other, that we wanted something more. Mark stood up, the boxers falling to the floor, and got some Vaseline from the bathroom. "Okay, boy, on your hands and knees on the bed!" I climbed up on the bed, my ass in Mark's direction. He smeared some Vaseline on his finger, and slid it in my ass crack and around my asshole. I felt him stand behind me, one hand on my hip, the other guiding his rock hard cock against my hole. He slid his cock across my hole as I spread my cheeks for him. This felt so strange, but I was getting hornier by the minute. "Okay, son, just relax. This is gonna hurt a bit." Mark slowly pushed his cock into my asshole until I felt a pop as the head slid in. "Ow, that hurts, man! Take it slow." "Sorry, try to relax. I'll go very slow." Luckily, Mark didn't have a very big cock. This would have been a killer with a huge one. Gradually, I felt him slide further inside, as I tried to relax and make room for him. My cock was iron hard, and throbbing, especially as I felt pressure on my prostate. Mark's hands were on my hips, slowly pulling me on him. "Oh, man, that hurts so good. Fuck me in the ass!" "Son, your ass is so tight! Tonight, I'll make you a man! Take my cock - all the way!" I could feel Mark's balls slap against my ass as he started thrusting. I never in a million years thought I would be doing this, but it was so erotic, the pain and pleasure mixed together. "Fuck my ass, sir! Give me your hot cum!" After a few more minutes of thrusting, Mark yelled, "Take my cum, boy!", and shot a hot load of sperm in my ass. I could feel the cum spurting in and leaking down my balls and legs. The pressure relaxed as Mark's cock went limp. He reached around and started stroking my hard cock. "That's a good boy. Now this is for you." He didn't have to stroke much at all, before I shot a thick load of creamy cum across his sheets. Mark pulled out, and we collapsed into each other's arms on the sticky bed, "Oh, man, that was so horny. Are you okay?" "I think so. I'll be a little sore when I sit for a few days. I hope it feels better soon - I want to do this again!" Mark laughed, "Yeah, me too! Next time you can wear the boxers and be the dad." "I should have asked my mom to get me some big men's boxers for Christmas instead!" 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?" Underwear Friends Ch. 04 As it got closer to graduation, Mark and I realized that our days together were coming to a close. His mom was thinking of moving back to Texas, and Mark was thinking of going to college there as well. I was accepted at a college in Wisconsin, so it was unlikely we would have many opportunities to be alone. Even our sometime shared partner, Cindy, was going on to school out east. Mark was my first lover, introducing me to boxer shorts, blowjobs, role playing and three-ways. No demands, no drama, just fun, sex and intimacy. We would be leaving on good terms, and it was somewhat bittersweet. After what would be our last time together, we each traded some boxers for a final time, for a final remembrance, We kissed and hugged, and I wouldn't see him again for 20 years. It was summer, and I was working as much as I could before going to college in the fall. I didn't have too much time to feel sorry for myself, but when I was home, I think I was a little moody. Mid-summer, my little brother, Tommy, was away at camp for two weeks, and my father was away on a business trip for the same two weeks. My mom had suggested that she and I take a vacation, but I had to work, so we would just hang out together once in a while. One morning, I was heading downstairs in just my paisley boxers to take a shower. I thought my mom was up in her room, so I was surprised to see her in the downstairs bathroom, putting clothes into the washer. As I walked in, she jumped and let out a yelp. I thought she had been sniffing the crotch of a pair of my boxers in the laundry basket. "Oh, Ray! I thought you were still sleeping. You scared me!" "Sorry mom, didn't mean to." Her eyes drifted to the boxers I was wearing, slightly askew and the fly partially open. I usually didn't walk around the house like that in front of my mom, and I moved my clean clothes in front of me to cover myself. "I was just sorting laundry. I try to look for stains and treat them before throwing them in." She was still holding a pair of my boxers, and I'm sure there was a cum stain in them. "Thanks, Mom," I replied awkwardly. "Do you want me to come back when you're done?" "No, that's okay. I'm almost done." She threw the remaining clothes in the washer. "If you give me those boxers, I'll throw them in too." She pointed the ones I was wearing. I didn't know what to do. She was my mom, but still very hot. And since Mark left, I was very horny. If I took off my boxers there, my boner would stand right up. "Ah, sure," I replied. I set down my clean clothes on the counter and climbed into the shower, shutting the frosted glass doors to a crack, then removed my boxers and handed them to her through the crack. "You know, I sure like your new boxers. That's the first time I've seen you in them - they look nice on you. You look so mature. Your father doesn't look that good in his, and Tommy hasn't filled his out yet." This was getting a little awkward. "Thanks for picking them out for me, Mom. The guys in school started switching to them, and they're getting more popular." "Glad you like them. I think Penney's is having a sale. Maybe I'll pick you some more up for school in the fall. What kind do you like the best? You have some with patterns. How about some pastels? Before Christmas, I saw some nice blues, greens and yellows." I didn't know where this was coming from, but I started getting aroused. I had peeked at her Christmas underwear, and saw nylon panties in those same pastel colors. My dick was getting erect, and I turned to the side in case she could see anything through the frosted glass. She was still standing there! "Yeah, that would be really great. I like pastel colors a lot." "Great! Anything else you need? More A-shirts? I think those look really good on you too." "Sure, Mom, more A-shirts would be great." "Ok. Take your shower then. I'm going to run some errands, so maybe I'll stop at Penney's while I'm out. If I see anything else you might need, I can pick it up. Then you can model it for me....well, except for the boxers....unless I happen to see you around the house in them again.... Start the washer when you're done. Thanks" She left the bathroom and shut the door. I looked down at my raging boner. What was I thinking? She was my mom! But she was going on and on about my underwear. Was she really sniffing my boxers?!? I finished my shower, dried off and got dressed. I remembered to turn on the washer, but before I did, I lifted the lid and sorted through the clothes in there. Mostly underwear and t-shirts, then I came across a pair of her pink nylon panties. Feeling a little guilty, I took them out and looked in the crotch. They were stained with pussy juice! She must have been horny, and rubbed herself off! I dug around a little more, and found three other pair, light blue, green and yellow, each with pussy stains in the crotch. Just like her comments about boxers. Was she fantasizing about me?!? Now I was getting aroused. I had to go to work, but I'd be thinking about this all day.... I called home during my break. "Hey Mom, how about if I take you out to dinner tonight? With Dad and Tommy gone, we should do something special. And you've been doing me a lot of favors lately, like picking up new underwear and stuff. What do you say?" She sounded surprised and a little excited. "Wow, that sounds nice! Kind of like a date, huh?" "Yup, wear something nice. I'm getting done early, so I'll come home and shower and we can go out. Do you have a special place in mind?" She thought for a minute. "How about Angelo's? They have great food, and your father will never take me there." "Sounds like a date. I'll call for a reservation for 6:00. See you tonight." I hung up the phone. I was sure she was excited over the phone, and I was surprised to realize that I was excited too. I got home, and ran upstairs to get clean clothes. Mom's bathroom door was closed, so I yelled, "I'm home! I got the reservations. I'm going to shower." Mom yelled through the door. "Ok, thanks! I picked up that new underwear for you, and washed and dried it all for you, if you want to wear any of them." Wow, this was getting better by the minute. "Thanks, Mom! I appreciate that!" I walked into my room to see a pile of six folded boxers and A-shirts on my bed. Just like she said, pastels of blue, green, yellow, some shade of light pink/purple, tan and grey. "Very nice colors, Mom! Any particular color you like the best?" "I like them all, but I think maybe the lilac the best." Lilac, that's what the pink/purple color was. "Cool, I'll wear those tonight. Ok, I'm gonna take my shower now." I ran downstairs and hopped in the shower. We had about 45 minutes until the reservation. I shaved, then dressed in khaki pants and a dress shirt. Mom was coming down the stairs as I got to the kitchen, wearing a pretty sundress, heels and nice jewelry. "Wow, Mom! You look great!" She blushed a little, "Thanks, Ray! You look very handsome yourself. People will think we're on a real date tonight." My mom was really quite attractive, now that I've seen her in this new light. My father was a lucky man, but he sure didn't seem to appreciate her. I walked her out the car and opened the passenger door for her, then went around the other side and got in. "You're really sweet to take me out to dinner tonight, Ray." She leaned over and gave be a kiss on the cheek. Not a quick one, not too long either. A promise of more to come? As we drove to the restaurant, she asked, "Do you like this dress? I just bought it today whe I was shopping for you. I thought it looked so summery and fun." She lifted the edge to show me, and I thought I caught a glimpse of her lilac nylon panties underneath. I almost swerved the car. "I like it a lot. And I think it looks very good on you, too. Wait until Dad sees it." "Let's not talk about your father tonight. I'm sure he's having his own fun wherever he is." That sounded bitter, so I let it drop and changed the subject. We arrived at Angelo's and had time for a drink at the bar before dinner. We made small talk, asking each other about our day. I hadn't seen my mom this happy in a long time. She really seemed to be enjoying herself. The waiter came and let us to our table. I had asked for a table in the back, a cozy one where young lovers usually sat. Luckily they were able to reserve it for us. We ordered a bottle of wine and looked at the menu. Mom seemed a little tipsy when the food came. Too much alcohol on an empty stomach. As we talked and laughed, she would lay a hand on my arm, or touch my hand - little things that lovers do. "You really are getting to be a handsome man, Ray. Any special girl in your life?" "No, Mark and I had hung around with Cindy for a while, but neither of us saw that as long term. We'll see who I meet in college." She seemed a little sad, but smiled and said, "That's a month away. Let's just talk about now." We finished the meal, making small talk again, but each of us thinking about how the night would go from there. We were both sending off signals, flirting with each other. She sure didn't seem like my mom, this attractive and sexy woman. We left the restaurant. "Do we have to go home so soon, Ray? It's a nice night, how about a drive?" "Sure," I told her. I drove out along the lake north of town. There were less street lights, and you could see the start clearer. "If this were a real date, where would you take your girl if you wanted some alone time?" "Well, since I don't have a place of my own, I would take her out to the make-out area near Eddie's farm." "Want to show me where it is? Just pretend I'm your date. I won't tell anyone else," she almost purred. Wow, this was it! I drove to the old farm, and down the dirt road. It was private property, but no one was currently living in the old farmhouse, and we all knew Eddie, who said it was okay. There were three other cars already there, so I turned off my lights to give us all some privacy. I pulled up to the edge and killed the engine. "Here we are, Mom." "Call me Sue." "Ok, here we are, Sue." She leaner over to me and ran a finger down my cheek. "Thanks, Ray. You are a great date." Then she kissed me softly and longingly on the cheek. I turned to met her, our lips touching, feeling the heat and desire. Sue put her hand on my face and pulled me closer. We kissed for quite some time, and she was very good at it. She seemed hungry and full of desire. I was getting very turned on by her willingness. "Want to move to the back seat, Sue?" I grinned. "I thought you'd never ask...." I turned off the overhead light, so when we opened the doors, there was no light. The quarter moon behind us gave just enough light in the back seat for us to see what we were doing. Sue lay back on the seat, and I reclined across her, all the while, still kissing. I ran my hand across her breast, and felt the hard nipple through her bra and dress. Sue gave out a little moan of delight. I tweaked her nipple and she squirmed under me. Reaching around the back, I unzipped the top of her sundress and slid it off her shoulder. I pulled her silky bra-strap off her shoulder, exposing her full breast. I had once sucked on these breasts as a child, and now was returning as a man. I took her nipple in my mouth, nipping at and flicking my tongue across the hard tip. Sue let out a deep moan. Freeing up the other breast, I alternated, feeling Sue get more and more aroused. She reached down, searching for my cock, and let out a purr when she found it straining against my pants. "I watched you through the shower door today, Ray. I could see how big your cock was. I wanted to suck you off right there. Did you know that?" she murmured in my ear. "I thought you were watching. I was so surprised and excited to see you like that." Sue laughed, "You haven't seen anything yet, my boy. I want one kiss on that cock of yours, then you're taking me home. There isn't enough room in this back seat for what I want to do with you tonight." She undid my belt, then opened my pants up. "Mmmm, sexy boxers! You got the hint - we're wearing matching undies tonight." Sue flashed me her lilac panties, then sat up and pulled the waistband of my boxers out and reached in. She pulled my cock out, throbbing in her hand. "Ray, this is such a nice cock you have! I haven't seen it since it was tiny, and now it's bigger than your father's." She leaned down and gave the head a kiss that felt like being struck by lightning. "Now, let's get back in the front seat, and get home." Sue put her dress back on, but when I started pulling my pants up, she exclaimed, "No, leave those open. I want to hold on to you all the way home." She gave me a naughty grin. We got back in the front seats, and I drove home. True to her word, she held on to my cock all the way home, occasionally pumping it to keep it hard. Once, when we pulled up at an intersection next to a cop, she smiled at him, but kept holding me below the level of the window, hoping he couldn't see. He didn't even look twice. We pulled into the garage and shut the automatic door. Sue got out of the car, and took off her sundress right there. She was standing in heels, her white shiny bra, and lilac nylon panties. "Quit staring, big boy! Let's go!" We entered the house, and she was on me. Kissing me hard on the lips, unbuttoning my shirt and sliding down my pants. We took off our shoes and she let me to her bedroom. Mom lit some candles, and we laid down on her and dad's bed, the sheets pulled back. I was wearing my white A-shirt and lilac boxers, she in her white bra and lilac panties. "Mmmm, very sexy. Matching underwear colors. I've been thinking about this all day, Ray. Ever since you caught me sniffing your boxers. Did you know you have some strong smelling cum stains? They get me horny every time I smell them. Sometimes I drop my pants and masturbate right there. And sometimes when your dad is away on a business trip, I sleep in a pair of your dirty boxers and masturbate myself to sleep. Did you know your mother was so naughty?" she grinned. "Mom, I mean, Sue, that is so hot! Did you know I sniffed your panties today when I started the washer? They were driving me crazy all day!" "Then, let's do something about it, Ray!" She rolled on her side and slid a hand up my A-shirt, squeezing my nipple. Sitting up, Sue pulled up my A-shirt, exposing both of my nipples, then leaned down to lightly bite them. I slipped my shirt off, then reached around to unclasp her bra. Sue's full breasts slid out, hanging over my face. I pulled her to me and returned the favor, lightly biting her nipples. We were both enjoying this immensely. With no one else at home, we could cry out when the other did something that felt particularly good. And we could talk dirt to each other. "I want to suck that big cock of yours!" Sue slid down the bed and pulled down my boxers. With one hand she cupped my balls, and the other, she pulled me into her mouth. She stroked and squeezed as she slid the tip and and out of her mouth, while massaging my balls. She pulled it out and said, "Good thing you young guys can cum more than once in a night. I'm gonna suck you off now, then you're gonna fuck me later, got it?" "Yes, m'am!" "Good boy, now, give me your seed!" She went back to massaging my balls and jerking me in her mouth. She was very skilled in this - I was totally amazed. She played with me for quite a while, before I finally lost it. "I'm cumming!" and shot a huge load right in her mouth. She gulped and swallowed all of it, gently milking the shaft to get it all out, then licking my cock clean. "Mmmm that is some good-tasting cum you have, boy. Tastes much better than it smells. Here, taste some." She leaned down to kiss me, and put her tongue in my mouth. I could make out the faint taste of my cum. "Now it's mommy's turn. I need a good eating out - it's been years since a tongue has been down there." She laid back on the bed, and I stuck my face down by her crotch. I could smell her strong musk, and see the dark damp spot in her lilac panties. I pulled one panty leg over and licked my tongue inside, brushing against her outer lip. It was dripping with her honey. "Oh, god, yes, Ray!" I licked here for a while, then moved to the other side. The crotch of her panties was so wet now that the sheets were getting a wet spot - all from her pussy juice. I put my mouth on her pussy through the nylon material and kissed it like it was another mouth. She squirmed and moaned in delight. A few minutes of this, and I gently pulled her panties off. We were both now totally naked. Her cunt was glistening in the candlelight. I want back to kissing it again and she almost jumped off the bed. "Don't stop! Don't stop!" I pulled her body toward the side of the bed, so I could kneel on the floor and get a better angle on her pussy. I ran my tongue around the outside, back and forth, then flicked it across the clit. I darted the tip of my tongue inside her honeypot, then again flicked across her clit. Soon, her clit was red and engorged, her pussy lips full and pink. There was salty juice all over her legs and my face. I ran my tongue around her clit in little circles, faster then slower, alternating with sucking on her clit. I listened for what she liked and made sure to go back to that. Variety in position and speed, giving all of my attention to her needs. "Oh, god, Ray! That feels so good! Eat me!" I kept it up until she started making little mewing noises and I could feel her legs starting to switch. She shuddered, then pulled my head tight against her pussy, yelling out. She twitched and her legs spasmed, and she pushed my head away to catch her breath. A stream of juice shot out of her pussy, almost like she was peeing. "Oh, that was so good! I haven't sprayed like that for years. You are truly gifted - where did you learn that?" Now wasn't the time to tell her about my extracurricular activities with Mark and Cindy. We lay back in each others arms, trying to get our breath back. She kissed me, then brought a wash cloth to cleanup the strong pussy smell around my mouth. "I promised you one more fuck tonight. Are you still up for it?" I looked down and saw my cock coming back to life. "I think I'm up for that, at least one more time." I smiled. She stroked my cock a few times until it was hard enough, then she got on her hands and knees so I could fuck her from behind. It felt so good, and she was so willing to experiment. On top, on the bottom, sitting, laying, sideways. We were growing tired, and ended up in the standard missionary position. As we slowly fucked, we kissed and caressed. Soon I shot my second load right into her pussy. She pulled me close, and I could feel her shudder as she came again too. We lay like that a while, me up on my elbows to take the weight off of her, until I got soft and plopped out. There was a gush of semen and cunt juice. We moved over a bit to avoid the wet spot, then laid there and talked. "Ray, you made me feel so special and young again. Your father and I haven't had sex for about eight years now. He isn't interested, no matter what I try. I think he's having an affair. I think that's what all of these business trips are. And I'm not sure I care any more." She started sobbing a little, and I held her tighter. "Mom, you are so smart and sexy and fun. Dad would be a fool to treat you like that. I'll always treat you like a lady." "Thanks, Ray. I guess I'm pretty lucky to have you, at least for a while." "Hey, Dad and Tommy are gone for another week and a half. We have a lot of time alone yet." "Then let's get some sleep. Tomorrow will be a busy day." 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....