Underwear Friends Ch. 06

Chris and I were really enjoying our freshman year in college. Our upstairs apartment was a few blocks from campus, and with school and our part-time jobs, we were pretty busy. But when we were home alone, we seemed to spend all of our time in various stages of undress or naked and exploring each other's bodies.

We slept together at night, usually in my bed, and used his bed as the 'fun' place. We were very intimate in private, and liked to wear each other's underwear as a way to stay close, even when we were apart. Chris liked to wear panties occasionally, and we liked to play in our underwear. In public, we acted like ordinary roommates, and didn't share our lifestyle with anyone.

Chris was a virgin before we started sleeping together, and I hadn't felt comfortable sharing all of my past sexual history yet. He knew I was bi, and that I had an intense relationship with a guy, Mark, from my hometown. He didn't know that I also had a brief sexual relationship with my mother the summer before I left for college.

My father had been cheating on her, and she finally found out and he moved out. She was a mess, but tried to hold it together for my younger brother and me. She hadn't had any intimacy or sex for a long time, and somehow after I broke up with Mark, our loneliness led us to some intense closeness and mutual pleasure.

I talked to my mom frequently, but hadn't felt like sharing my relationship with Chris yet. I don't know if I wanted to avoid making her jealous, or just didn't want to bring up any memories for her. Shortly before Christmas, my mom called and said that my brother would be staying with my dad for a week, and she wanted to come to Wisconsin to visit me. She would get a hotel, and we could hang out. She didn't mention our summer romance, but I could tell she was thinking about it, and judging from the growing sensation in my boxers, I was too.

I told Chris she would be coming to visit, and he offered to let her have his bed, but I didn't think I was ready for that yet. I wanted him to meet her, and thought we could go out to dinner, but he had to work late Friday night. I had off Friday afternoon, and was going to clean the apartment. My mom was expected to get to town around 6 and pick me up for dinner.

Friday came around, and while at school, I had to stay later than I wanted to meet with my group about a project we were working on. I wasn't sure how long I would be, so I called my mom hoping to catch her before she left. I got her voicemail, and said I might be late, but to let herself in the apartment, and that there was a spare key hidden behind a wall decoration by the door.

My group meeting dragged on, and I finally got to our apartment around 5:30, and was surprised to find both my mom and Chris sitting in the living room. They were laughing and hitting it off.

"What are you guys doing here?" I asked.

"I thought I would surprise you, Ray. I left early and then got your message, and let myself in. Chris showed up a little later."

My mom looked over at Chris, and they both had big grins, like they were sharing some secret. Probably about me or something.

"Yeah, Ray, I was able to get off work and thought I would take you up on your offer for dinner. I came home and thought I heard you, but it was Mrs. H."

Things seemed a little weird between us, but my mom and Chris seemed to be having a great time, so I went along with it, and we went out to dinner together.

I had made dinner reservations for a cozy Italian restaurant that I had never been to, but heard good things about. During our summer romance, I had taken my mom out to a nice Italian restaurant in our hometown, and was kind of thinking that I might see what happened tonight. I was a little miffed that Chris came along, because now I knew for sure I wasn't going to rekindle any heat with Mom.

The restaurant was indeed cozy, a little dark, with lots of nooks and angles to give the diners a sense of privacy. They were able to add a third to our reservation, and the waiter sat us in a corner booth, my mom sitting between us. She ordered a bottle of wine and some bread and olive oil, and the conversation flowed.

All through our talk, Chris and my mom were making little smiles at each other, which turned into giggles as the wine went down.

"What's going on with you two?" I asked.

"Oh nothing, Ray! We just hit it off right away while we were waiting for you to get home," my mom replied. She moved her hand under the table and caressed my thigh, and I felt my cock twitch.

We ate dinner and continued talking, all in fun. My mom rubbed my thigh often, moving higher until she felt my erect cock, and gently ran her fingernails across the bulge. I was really hoping I could go to her hotel room after we dropped Chris off.

After dinner, as we were getting in her car, she asked, "Would you boys like to see my hotel room? Maybe we could swim in the pool."

"I don't think Chris needs to do that, do you Chris?" I asked.

"I think it would be fun, Mrs. H. Is that ok with you, Ray?"

I started fuming, but didn't know what to say. After she got me all horned up, I just wanted to undress my mom back at her hotel.

My mom and Chris looked at each other and laughed out loud.

"Do you think we should tell him?" Chris asked.

"Oh, I suppose so. Otherwise he'll sulk," my mom laughed. "Chris, we have a really funny story to tell you..."

She started the car, and drove to her hotel.

"You see, I thought you would be home this afternoon, before you had to work on your project. I left town early, wanting to surprise you for some afternoon delight before dinner."

"Mom! What are you saying? Chris is here!"

"Oh, Ray, Chris knows all about us. He's part of the story."

I just about shit myself. I wasn't ready to tell Chris. What would he think of me?

"I got to your apartment, and used the hidden key to let myself in. By the way, that was a hard key to find. I almost pissed my pants looking for it!"

"Anyway, I got in and neither of you were home. I toured your apartment, and figured out which bedroom was yours. I found some of your boxer shorts in your dirty laundry basket and couldn't help myself, so I took them out to smell them."

"Mom! You're embarrassing me!"

"Ray, this is hilarious! Mrs. H already told me all about this while we were waiting for you."

So that's what they were laughing about.

"Just smelling your boxers brought back all those hot memories we made this summer, and I couldn't wait until you got home. I decided to strip down to my underwear and wait for you on your bed. I was hoping you wouldn't be long."

I couldn't believe this. I put my head in my hands. My mom was saying all this in front of Chris. What was he thinking?

"I was getting very horny, and started playing with myself. I decided to leave you a clue, so I took off my bra and panties and hung them on the chair in the kitchen by the door, so you would see them as soon as you got home."

This just kept getting better and better.

"I went back to your room, and started playing with my pussy on your bed."

"Mom!"

"That's where I came in," Chris continued. "You had asked me to meet your mom for dinner but I had to work. After school, I was able to get someone to swap a shift for me, so I came home to wait with you. I walked in the door and saw a bra and panties on the chair. You know how much I liked the panties you got for me, and I thought you bought me another present."

"Chris! My mom is here!"

They both laughed.

"Ray, she knows all about this too. We had a long talk before you got home."

This was killing me.

"Anyway, I thought the bra and panties were for me. I heard some noises from your room, so I expected you were waiting for me there. I stripped down like I usually do when I get home, and quietly put them both on. The panties were very sexy, beige with a lacy waistband, but a little loose for me, Sorry, Mrs. H. The bra was white and lacy, and also a little loose for me. I had never tried one on before, and didn't quite know how to put it on and hook it. I got it mostly on, and crept down the hall to your room. I opened the door and yelled, 'hi sexy!'"

"And that's when I screamed! I had expected you, Ray, to get the hint about my underwear, and to find me naked on my bed waiting for you. Here was some other guy, and he was wearing my bra and panties!"

I held my head in my hands.

"I backed away from the door, almost falling over myself. Mrs. H came out wearing a sheet, and we introduced ourselves," he laughed. "After a few minutes, it became obvious that we were each expecting to have sex with you, so we talked it over. She told me about your summer, and I told her about our fall. I explained how much I liked wearing panties, and that I didn't know how to put on the bra. Mrs. H showed me how to put it on and take it off, and after a few times it was easy. We decided we better get dressed, and find a way to break it to you."

We arrived at the hotel, and began walking to her room.

"Are you mad at me, Ray? I'm sorry, I just wanted to spend some more time with you. You make me feel so good when we're together."

"No, I'm just surprised, that's all. I thought you two were conspiring against me, but I guess this is a good way," I laughed.

"Good, because we both expect some action from you tonight, mister. We thought it would be better to come to my hotel because I had a king-sized bed, and we were going to need the room for all of the sex!"

We entered the side entrance, and talked up the stairs to the third floor. Mom unlocked the door, and we all entered the room. It had a big king bed, small couch, chair and coffee table, with a big TV.

"Chris, honey, do you mind if I go first? You're had Ray more recently than me, and I really need to get some of that cock of his."

"Of course, Mrs. H. Just leave some for me!"

I couldn't believe what I was hearing, but I was so horny now, that I was game for just about anything. Mom came up to me and gave me a long kiss. We hugged each other tightly, and kissed passionately, tasting each other's lips.

"Have a seat, Chris, and enjoy the show!" Mom called over to him. Chris took a seat where he had a good view or Mom unbuttoning my shirt and taking it off, then lifting my A-shirt over my head, and caressing my nipples.

I glanced over at Chris, watching us intently, and gave him a big grin.

Mom caressed a hand along the bulge in my jeans, then kneeled in front of me. She began undoing my belt, then opened my jeans and pulled them down.

"Mmmm, sexy boxers! I don't recall buying these for you. I like these grippers!"

Mom pushed my jeans around my ankles, then helped me get my tennis shoes off so she could get my jeans and socks off.

"Chris, you can start taking off your clothes too. I'm going to want to watch the two of you later!"

Mom unsnapped the grippers of my boxers, and my erect cock plopped out.

"Oh Ray, I really missed seeing you and your beautiful cock. I hope Chris has been taking good care of it!"

She dropped my loose boxers to my ankles, and I stepped out of them. I was totally naked now, and Mom took my hard cock to her mouth and licked the tip. She slid the head in her mouth, gently running her tongue around it. All of those erotic memories of the summer came flooding back.

Mom took my cock deeper in her mouth, sliding it in and out, sucking and working her mouth around the shaft. I glanced over at Chris, who was watching with wide-eyed concentration. He had stripped to just his light blue panties, and was rubbing his firm cock through the soft material.

"Better slow down, Mom, or I'm gonna blow a load right now!"

"We wouldn't want that so soon, would we?" she giggled. "Chris, come on over here and take over so I can get more comfortable."

Chris obeyed, and kneeled in front of me, taking my hard cock in his mouth. Mom went to the bathroom, and came out wearing just her white bra and tan panties, which must have been what started the whole evening.

She kneeled down next to Chris, and took my cock in her hand, moving it between both of their mouths and taking turns sliding it in and out. I was getting sensory overload from my cock.

"Mom, I need a break before I shoot my load! I think it's your turn now."

I pulled out of Mom's mouth, and guided her to the bed. I pulled back the covers and Mom laid on her back. I crawled up next to her and gave her some passionate kisses.

"Chris, come on over here. I think Mom can use some extra attention tonight."

Chris looked from me to Mom, and asked, "Is that ok, Mrs. H?"

"Of course, honey. After all, you've already seen me naked, and worn my underwear."

Chris laughed, and climbed up on the other side of Mom. She took his face in her hands, and pulled him close for some serious kissing. While they did that, I ran my hands over Mom's bra, playing with the lace, and slipping my fingers under the straps and sides. I bent down to kiss her nipple through the material. Chris saw me, and did the same to the nipple on his side.

"Mmm, I like this attention, boys. Would you like me to unhook my bra for you?"

"Let me, Mrs. H! I'll show you how I remember your lesson from this afternoon."

Mom raised her back a little, and Chris reached under with one arm, and after a few minutes, her bra popped loose. I slid my hand under the material, and cupped her right breast. Chris helped slide the bra off her arms and tossed it to the edge of the bed. I bent down and took her right nipple in my mouth, feeling the hard tip in my lips. Chris took her left nipple in his mouth, and we both suckled like newborns.

"Oh god, boys, that feels so good! Both tits at once!"

We worked on her for a while, and began running our hands over her warm skin. I reached down to caress her panties, playing with the silky nylon material. Mom moaned when I reached down to slide my hand across her pussy.

"Mom, you are SO wet down here. Your panties are soaked!"

Chris slid his hand down to explore what I was describing, caressing my hand and Mom's pussy.

"Mrs. H, these weren't that wet when I was wearing them earlier."

"You boys are getting me so horny! What I want right now is some tongue in my pussy!"

I grinned at Chris, and we moved down to the end of the bed. Chris took the lace waistband of the tan panties and pulled them down, sliding them off her feet, and tossed them by the discarded bra.

I put my mouth between Mom's legs, and gave her pussy a long kiss. She groaned in delight. I moved my mouth around, kissing it like it was her mouth. I moved to the side, and gave Chris a chance to do the same thing. He had told me he had never seen a pussy close up, so I made sure to give him plenty of time to explore. She had shaved her pussy and left a little trimmed patch of pubic hair at the top for us to play with.

We alternated kissing and licking her pussy, and occasionally kissing each other on the mouth. Mom moaned as we got her more and more worked up. I showed Chris how to flick her clit with my tongue, and suck on the aroused hood. He was a natural, and really worked hard to make sure she was enjoying his efforts.

"Oh boys, I need some cock inside me right now!"

I climbed in place, and grabbed the shaft of my cock, and slid the head up and down across her engorged pussy lips. I could feel the heat of her pussy on my cock head. I guided my cock into her waiting pussy, and slide it inside. She was so wet and aroused, that it easily slid in all the way.

"Oh god, Ray! That feels so good! Fuck me, baby! Fuck your mother!"

I moved my cock in and out of her pussy, speeding up and slowing down, and getting into a strong rhythm. I started pumping in and out.

"Faster, baby! Fuck me! I've missed your beautiful cock!"

I glanced at Chris, who was staring at us, rubbing his cock while still wearing his light blue panties. He looked up at me and smiled.

I could feel myself reaching climax, and tried thinking of other things to hold off for Mom.

"Oh yeah baby! Fuck me! I'm close! Give me your seed! Cum in my cunt!"

I knew Mom had had her tubes tied, so I could shoot my load inside without worry. I could feel the pressure building, and kept pumping.

"Oh yes! Give me your boy seed!"

I couldn't hold it any more, and my cock exploded in her warm wet pussy. Spurt after spurt of thick cum shot out. I could feel her getting even slicker and I had to slow down so I didn't pop out. I slowed my strokes, shooting out every drop of cum.

"Aaaaaaaaaaaaaaahhhhh! Oh yes! YES!....."

Mom hugged me tight as I stopped thrusting, and I laid across the top of her.

"Oh baby, that was so good! I missed this so much!"

"Me too, Mom. I missed you and this. I love you."

"I love you, too, baby."

We looked over at Chris, and Mom said, "Get over here, Chris, we want to hold you too."

Chris smiled, and lay along us, and we both pulled him in close.

We laid like that for a while, until my cock softened, and I plopped out. I slid off her to the side, and the three of us just held each other.

"Chris...I'd like you to make love to me too. We've gotten so close today, I want to take your seed too."

"Um...wow...I'm not sure...I've never done that before...I don't think could compare to Ray..."

"You don't have to if you don't want to, but you would do fine. Ray has just had a lot more practice, haven't you Ray?"

I grinned. "Yeah, the first few times with Mark I think I only lasted 10 seconds."

"Ok, Mrs. H, I would really like that."

"Say it like you mean it."

"What do you mean?"

"Say you want to fuck me!"

"Um...is it ok if I...fuck you?", Chris hesitated.

"Yes! But say it like you mean it! Say you WANT to fuck me!"

"Ok. Mrs. H., I want to fuck you! Right now!"

Mom giggled. "Yes, that's great. Take me, Chris! Ray, help him out."

I stroked the front of Chris' panties, and helped him take them off. Now all three of us were naked.

Chris climbed up between Mom's legs and leaned forward. I stood behind him, and put my hand between Chris' legs, and stroked his balls, gently playing with the pubic hair on them. Then I reached forward, and grabbed his hard cock. I slid his head along her wet pussy lips, letting him feel the soft and warm hole, still slick with my recent cum.

He moaned as I played with his cock at the entrance to Mom's pussy. Then I slid the head inside, and cupped his cute ass to push him all the way inside.

With my hands on his hips, I helped push him in and out, setting up a rhythm I know Mom would like. Chris moaned in pleasure.

"That's good, Chris honey! Fuck me with your big cock. Feel Ray's seed inside me, and give me your own seed now."

Chris was doing fine on his own, thrusting and concentrating on pleasing Mom and not blowing his load. I let go of his hips and moved to kiss Mom on the lips. I stroked Chris' back encouraging him. I moved back down to his cute ass and kissed his soft cheeks. We had never fucked, and never even talked about it before. Mark and I worked up to it, and I figured Chris and I would at some point too.

I took the opportunity to run my finger along his ass crack, pausing to tickle his asshole and taint. I didn't think he would be able to keep fucking my mom for long, so I wet my middle finger, and explored his hole. I gently inserted my finger to the first knuckle, and massaged Chris' hole from the inside. He jumped a bit but kept on fucking.

"Oh yes, Chris! That feels so good! Your cock feels so good in my pussy! I want you to fill me up with your hot seed, Make a mess inside me."

"Mrs. H, you are so hot! I can't hold it much longer..."

"That's good, baby! Let it go! Give me your seed!"

I kept massaging his hole, and slipped my finger in a little more, still helping push him in and out of my mom's pussy.