Underwear Friends

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."