Jack and I have been best friends for as long as I can remember. We are actually more like brothers than friends. Neither of us have siblings, so we probably subconsciously rely on each other to fill that gap in our lives. When we graduated from high school, we joined the Navy together. After we finished our schooling, we were assigned to different ships and went our separate ways.
Jack and I wrote to each other for awhile but the letters eventually stopped coming. A few days before my enlistment ended, I bumped into him in the Enlisted Men's Club at the Norfolk Navy Base. If not for that fortuitous turn of events, I probably would not have a story to tell. Because we had enlisted at the same time, our enlistments ended at the same time. Jack was as eager to get out of the Navy as I was. We celebrated a little too hard that night.
Jack bought an old jalopy for the drive home and invited me to ride along. By sharing expenses and driving, we both saved money. After an uneventful trip, Jack and I pulled up in front of my house. I insisted that he come inside to get reacquainted with my mother.
I wasn't prepared for what I saw when Mom opened the door. She had always been very attractive, but while she was married to my father she didn't pay much attention to her appearance. But after the divorce, she reinvented herself. She trimmed off a few pounds, bought some stylish clothes, and had her hair done in a trendy style. Standing in the doorway was one of the sexiest, most beautiful women I had ever seen.
Mom and I held our embrace a little longer than is proper for a mother and son. She wasn't wearing a bra and I could feel the warmth of her big soft tits through the thin material of her blouse. She gave Jack a friendly hug and invited him in. She ushered us into the kitchen and served us frosty bottles of beer. Jack could hardly take his eyes off of her. I should have been pissed at the way my buddy was ogling my mother's cleavage and ass, but I only felt a growing sense of excitement. Jack declined Mom's invitation to stay for dinner. The first thing she said after he left was, "Your friend is certainly handsome now that his skin has cleared up."
Over dinner, Mom told me all about what she called her "brand-new life". She had gone into real estate sales and had become very successful. That explained the designer clothes and the expensive new furniture throughout the house. She insisted that I live with her for as long as I liked, and that I take my time in finding a job.
Mom and I chatted as we watched TV together. Her perfume was very distracting and so was everything else about her. I got a hard-on whenever she crossed the room. She had learned how to do a "model's walk" and it really was hot. That night in bed I had to jack off twice before I could get to sleep.
Jack called the next day and asked me to meet him for a few beers at Clancy's Tavern. We shot some pool, watched some baseball, and put away a few drafts. I could tell that my friend was eager to change subjects, and he did as soon as we settled down in a booth for some serious drinking.
"Damn, Larry, your mother is drop-dead gorgeous," he said. "I remember that she was a babe when we were in high school, but she is really something now. My Mom looks a lot hotter now, too, since she got rid of Dad."
He pulled a picture out of his shirt pocket and handed it to me. I immediately recognized Jack's mother Stella, even though there had been many changes in her appearance since I had last seen her. She was at the beach clad in a modest two-piece bathing suit that showed off her curves to perfection. She had struck a sexy calendar-girl pose for the camera.
"Damn, Jack, I'm getting a hard-on," I confessed.
"That's okay, buddy. I got more than one while I was checking out your Mom. I had to jack off before I could get to sleep last night."
"Yeah, me, too. Can I keep this picture to jack off with?"
"Sure, keep it. Look, buddy, I have a great idea," he said. "Mom's birthday is tomorrow and I'm taking her out to a nice restaurant for a fancy dinner. Why don't you guys come along?"
I accepted his invitation and the four of us met at the best restaurant in town. I struggled not to ogle the blonde bombshell sitting across the table from me. The picture Jack had shown me didn't do her justice. Damn, was she hot! Mom (her name is Connie) and Stella had been casual friends for years, but that night they really bonded. By the time we finished our coffee and went to the bar for drinks, they were like best friends. As we wound our way through the tables, every head turned in our direction. I thought my chest would burst with pride.
Mom invited Jack and Stella back to our place for drinks. When Mom found out that Stella was a Bridge player, she insisted on a game. Bridge was one of Mom's favorites, too. Those two certainly had a lot in common. If Mom and Stella had any faults it was that they were a little too free with the bottle. Both of them got a little tipsy, and Jack and I swapped winks when Stella asked us if we had visited any whorehouses while we were in the Navy. It just kept getting better and better.
Our Bridge games became a regular weekly occurrence. Jack and I hated the game but we played because it gave us an opportunity to ogle our mothers. As soon as the girls had a few drinks in them, they began to flirt with us. Stella was fond of using not-so-subtle double-entendres to tease me. I had to struggle to concentrate on the game and to keep my dick from rising.
Jack and I were at Clancy's one evening having a few pints and shooting the breeze. "The next time we play cards I'm going to make a run on your Mom," he said. "Do you have a problem with that?"
"Hell, no, as long as you don't mind me making a run on yours."
We came up with a devious plan. Our Bridge games always stopped promptly at ten so Mom and Stella could watch their favorite nighttime soap. I always taped the program in case Mom missed any of it because of a phone call or other interruption. I loaded a porno tape into the VCR beforehand, and when I pretended to start recording Mom's program, I hit the play button instead. The soap opera disappeared and was replaced with a raunchy orgy scene.
"Oh, my God, I'm so sorry," I said. "I was watching that this afternoon and forgot to take it out. I'll turn it off."
But before I could hit the stop button, Stella said something that Jack and I had been hoping to hear.
"Oh, no, leave it on. I've heard about these but I've never had an opportunity to watch one. Let me satisfy my curiosity."
Sitting beside my mother watching porno was the wildest thing I had done in my life until then. The tape was really hot, and I wished that I had chosen something a little less raunchy. But it worked just the way Jack and I had hoped. Mom and Stella began exchanging comments about what was happening on the screen.
"Wow, what a mess," Mom said, after a very sloppy cum-shot.
"Yeah, that thing was like a firehose," Stella said with a giggle.
We watched the entire tape, and Mom and Stella loved it. Jack looked over at me and winked. I could see that he was terrified. I wondered if he could overcome his fear enough to make his move. He rose to his feet and stumbled toward Mom. His dick was so hard that he couldn't walk upright.
"C..c..c..come on, C..C..Connie," he stammered. Mom's jaw dropped and she looked over at me. I didn't see anger or shock on her pretty face, only the same look she gets when someone pays her a compliment.
"Don't look at me, Mom," I said.
Mom got to her feet and led my best friend to her bedroom. Stella and I sat quietly for a few minutes, and then she began to giggle.
"Well, wasn't that special?" she said. "Well, it's just you and me, Larry. I don't suppose you would be interested in screwing an old hag like me, would you?"
"You're one of the most beautiful women I've ever seen, Stella," I said. Then I took her by the hand and led her to my bedroom. She let me undress her, and I felt her up at the same time. Her tits weren't especially big, but they were just the right shape and had the right amount of sag. I finally had her down to her panties. I knelt in front of her and yanked them down. My cock nearly ripped through my zipper when I saw the full bush on her pussy. She grabbed me by the ears and pulled my face right into her sweet-smelling snatch. I ran my tongue up and down the slot and swirled it around the nubbin at the top. I hoped that my enthusiasm would make up for my lack of experience.
"Oh, yes, baby," she said. "I love that long, silky tongue. I really look forward to teaching you how to eat pussy with finesse."
She flopped down on the bed and spread her legs. I nearly broke one of mine getting out of my pants. I tried to mount her but she pushed me away.
"You wouldn't last a minute, baby, and I need a lot more fucking than that. I'll suck the first one out of you. Once we get that one out of the way, I'm sure you'll last longer."
Stella's mouth was warm and very wet. I had had my cock sucked by a few whores while I was in the Navy and a couple of sluts in high school, but none of them had been as good as Stella.
"Grab me by the hair and push my head up and down," she demanded. "I like my sex a little rough."
If I hadn't done as she asked, I probably would have lasted a little longer. I grabbed a handful of her hair and pushed her pretty head down on my cock until it hit her throat. That sent me over the edge.
"Oh, fuck, Stella, here it comes. If you don't want my load, you had better get off of me now."
I came so hard I saw stars and heard ringing in my ears. It just went on and on, and the entire time, I was pushing and pulling that slut's head up and down on my cock. She finally lifted her head and smiled at me as she swallowed my load.
"Damn, you really needed that, didn't you, hon? You should masturbate more often. It's not healthy to let your balls fill up like that. Now get over here and fuck me before your dick goes soft."
I mounted that beauty and shoved my cock into her hot, wet snatch. She immediately planted her feet for leverage and bucked up against me. She was much tighter than I expected and she had excellent muscle control. Each time I pulled back, her cunt tightened down on me as though trying to keep me inside. I was so naïve that I didn't even know that women can, with proper exercise, control their cuntal muscles.
Stella began raking her fingernails very lightly up over my back and ass. Then she wrestled me onto my back and impaled herself on my cock. I was amazed that such a petite woman could be so strong. I had never been in the woman-on-top position. I immediately saw its advantages. Stella's tits were swinging to and fro in front of my eyes. She grabbed one and stuffed the nipple into my mouth.
"Oh, you sweet son-of-a-bitch. You have a humdinger of a cock. It's been ages since I've had one as big and hard as yours is. I am going to wear you out tonight, boy."
After that outburst, Stella had her first of many orgasms. I was a little disappointed that she didn't make more noise. I wanted my buddy to hear what a good job I was doing on his mother. She screwed her eyes shut, nibbled incessantly on her lower lip, and tossed her head from side-to-side.
"Oh, fuck, Stella, I have to cum. What should I do?"
"Shoot every drop of that hot jizz into me."
I continued pounding my cock into her as my load shot out. Her slick cunt got even slicker as my juices mingled with hers. She was in the middle of a strong orgasm and was clamping down on me. She finally went limp on top of me.
"Keep it in me for as long as you can," she whispered. I managed to stay plugged in for five minutes or so, and then a strong contraction pushed me out. When Stella had said that she was going to wear me out, she hadn't been kidding. We must have fucked in twenty different positions. I didn't know there were so many different ways to fuck. The bitch made me cum six times before she rolled over and went to sleep. Stella was gone when I awoke the next morning, so my morning wood was wasted on jacking off.
Jack called me the next day. He was so excited that his tongue was tripping over his words. We agreed to meet at Clancy's after work. His eyes were glassy and he was grinning like a Cheshire cat. We grabbed a couple of mugs of beer and took a table in a far corner where we could talk.
"Man, is your mother a hot piece of ass," he gushed. "You won't believe some of the things we did to each other."
"Okay, calm down. I want to hear everything you did to my mother, starting at the beginning. Don't leave anything out."
"Well, she started sucking my dick as soon as we were in bed and she did it so good that I shot my load in about fifteen seconds."
Jack went on to tell me in graphic detail about every act he and Mom had performed. I sat there with an aching hard-on and took it all in. His story ended with a shocker.
"I fucked your Mom in the ass. Hell, she liked it just as much there as in her pussy. I didn't even ask her if I could do it. My cock slipped out of her pussy and when I tried to get it back in the tip got lodged in her ass-hole. I figured I might as well go for it so I pushed it in. Man, she went nuts."
I almost creamed my jeans when he told me about that. I vowed that the next time I got Stella in bed I would go for her ass. Then it occurred to me that the women might feel guilty about what they had done and not let us fuck them again. I needn't have worried.
We had our next Bridge game at Stella's house. When it was over, she took me by the hand and led me to her bedroom. Jack took Mom to his room. The second time was even better than the first.
"I suppose you and Jack have told each other all the juicy details," she said. He and I had agreed not to tell them about that. "No, I would be too embarrassed to do anything like that." A little while later I got my first piece of ass. A thousand fantasies had not prepared me for the feel of it. I did her doggy-style so I could watch my cock going into that beautiful, round ass. Each time I pulled back she clamped down on me. I didn't even last a minute.
"Don't feel bad, hon. All guys come too quick when they get their first piece of ass. You'll do better next time."
Stella gave me a fine education in sex that night. After hours of sucking and fucking in a variety of ways, she ordered me to jack off for her amusement. I had always wanted to jack off in front of a woman. I decorated her nipples with the small quantity of jizz that I managed to jack out.
Our sexual relationships with each other's mothers continued for several months. One evening Jack and I were at Clancy's filling each other in on the things we had done to our mothers the previous night. Right out of the blue, Jack made a shocking proposal.
"I think we should fuck our own mothers."
"No way, man," I said. "We've got a great thing going. Why should we do anything that might screw it up."
"Well, I'm going to go for mine. If you don't want to go for yours that's your problem."
Jack had already come up with a plan. I decided that the least I could do was hear him out. I had almost a full week before the next card game to consider his proposal.
The big night finally arrived. As soon as the card game ended, Stella and I went to my room to get it on. She liked to start things off with a blow job, but I told her I wanted to practice cunnilingus. I worked on her tits for fifteen minutes. By the time I headed South, her nipples were as big and hard as bullets. I buried my face in her muff and took a deep breath. She smelled like honeysuckle, one of my favorite scents. As I worked my tongue around in her pussy, I tried to remember all the little tricks she had taught me. I knew they were working when she began to moan and squirm around on the bed. Everything was going according to plan. Jack was also practicing his foreplay on Mom.
Jack and I had decided that thirty minutes of foreplay would be enough. Exactly thirty minutes after I took one of Stella's nipples in my mouth, I excused myself to go to the bathroom. Jack was already waiting in the hallway. I hadn't seen him naked since we went through Navy boot camp together, and I had never seen him with a hard-on. His cock was so hard it pointed at the ceiling. The lower half of his face glistened with Mom's sex juice.
"I got her ready for you, buddy," he said. "You shouldn't have to work too hard to make her cum. Good luck."
We shook hands and then I headed for Mom's room with my rock-hard cock pointing the way. I pushed open the door and peeked inside. Mom was on the bed rubbing her pussy. My heart raced as I walked toward her with my cock bobbing in front of me.
"Stella and I figured it was just a matter of time before this happened," she said. "Well, come and do it while we're both in the mood."
I mounted her and speared her pussy with one perfect thrust. Jack had done a good job on her. She responded immediately and bucked up against me. I forgot everything Stella had taught me about fucking with finesse and gave Mom the ramrod treatment. She began gasping and wheezing as my cock did its job.
"Oh, yes, that's so good," she whispered. "I like it hard and fast sometimes. Yes, that's it, give me more like that. YOU'RE MAKING ME COME! UHU..UHU..UHU..I'M COMING!"
Mom dug her fingernails into my ass as mini-convulsions rippled through her beautiful body. She wrapped her long legs around mine and crushed me in an embrace. Hoping to get her multi-orgasmic, I continued fucking her with short strokes. Feeling her shaking beneath me was the best feeling I had ever had. She was enjoying her fourth orgasm when I shot my load into her. I felt like a king!
Mom was just as insatiable as her girlfriend and we stayed at it until I couldn't get it up. The next morning the four of us had breakfast together, something we had never done before. Stella had that glow that some women get after they've had an especially good fucking. I could see that Jack was quite pleased with himself. No doubt my pride was showing, too.
"Well, I guess there isn't any reason we can't have a foursome now," Stella said.
We had our first foursome the following week. Jack and I had the pleasure of watching our mothers go the lesbian route. They had gotten to each other before we got to them. I'll tell you about it some other time.