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.
