A few months back, my husband left me for a much younger woman. I got the house, a ton of alimony, and a complete loss of self-confidence. Getting dumped by a man you’ve been loyal to for more than two decades has that effect on a woman. My daughter and friends tried to cheer me up, but nothing worked. I was miserable.
Then, about a month ago, my friend Linda called to ask if her son could stay with me. He had just graduated from college and was looking for a job in my city, and she wanted to know if I could put him up to help him save a bit of money. She said he could pay rent, but he just couldn’t afford to get his own place until he found a decent job. I told her he could stay with me for free. I said it would be nice to have a man around the house again, and as long as he didn’t mind helping me with some chores now and then, he could stay as long as he needed. She thanked me like any grateful mother would.
When I told my neighbor and best friend, Jessica, the first thing she asked was if he was cute. I said I had no idea since Linda lived halfway across the country and I hadn’t seen her son, Charlie, since he was maybe 10. Jessica said she was a bit wary of the idea of me taking him in, but I told her that Linda had assured me her son was a nice guy and kept out of trouble.
Jessica was over for a cup of coffee when Charlie arrived a few days later, and her leeriness turned to excitement the moment he stepped through the door. Charlie was a real hunk—tall, dark and very handsome. He was also extremely polite and friendly. When I showed him to his room, he was overjoyed. He asked if I was sure he couldn’t pay any rent, and I assured him that what I really needed more than money was a guy to do the heavy lifting since it was just us girls around. He said he’d help me out with whatever I wanted, all I had to do was ask.
After settling in, we got acquainted with one another. Charlie was almost as charming as he was handsome, and I knew things were going to work out. Jessica told him that she was delighted he’d be staying with me and helping me out, and I agreed.
Charlie turned in a bit early that night since he’d been driving most of the day. Jessica was still at the house, helping me clean up from dinner, and as soon as he was gone, she and I chatted about my new houseguest. She went on a great deal about how attractive he was. She even went so far as to openly wonder about the size of his cock. Jessica has always been, shall we say, “open” when she’s interested in a guy, so I insisted that she behave herself around him since he was going to be living with me. She scoffed at that idea, saying it would be such a terrible waste to have to behave around a guy as hot as Charlie. She really is irrepressible, and I knew that I’d have to keep a close eye on her.
Jessica then asked my opinion on his looks. I reluctantly conceded that he was very attractive. She then scandalously suggested we both take a crack at him. I was shocked at her statement and said as much. She pointed out that I hadn’t been with a man in quite a while, and Charlie was quite a man. It was apparent I was miserable, she said, and banging a hunk as good-looking as him was a surefire way to lift my spirits, so there was nothing wrong with taking advantage, should such an opportunity present itself.
The best I could come back with was that he’d have no interest in an old woman like me. Jessica then confided that she’d caught him checking me out when he thought neither of us was looking. That struck me speechless. I could see him being interested in my neighbor because she’s only in her late 20s, but I had gone to college with his mother! But the way Jessica said it meant she was being serious.
My mind was really awhirl. When I went to bed that night, I dreamt about my new houseguest doing all sorts of sordid things to me. At one point, I woke up from how aroused I was. It was the first time I had felt so excited in a very long while.
It took about a week before everyone settled into a routine. Jessica was true to her word and flirted with Charlie when she was at the house. I even caught her trying to peek when he was in the shower, though she claimed she thought he’d already left for his interview and didn’t know he was in there, despite the running water.
As for Charlie’s behavior toward me, at first he was a bit formal, but as we grew used to one another, we became more casual. I found him sincere and basically a good guy, which only added to his appeal. While I didn’t catch him checking me out, he always seemed to enjoy spending time with me, and I know I felt the same. His presence had quite the effect on me, and my dreams became increasingly hot and raunchy.
Things came to a head late the next week. Charlie had a couple of job interviews that would keep him busy until early evening, and once he headed out, Jessica came over and suggested we work on our tans by the pool. Since I have a tall fence, privacy isn’t usually an issue, but now that I had a houseguest, it was different. I might have been a bit self-conscious if Charlie had been around, but since he would be gone all afternoon, I could rest easy.
I slipped on my tanning bikini, which was definitely a bit smaller than a regular one, and joined Jessica to lounge by the pool and soak up some rays. We’d been out there for a couple of hours when a deep voice said, “It looks like someone’s enjoying the afternoon.” It was Charlie, in a pair of swim trunks. While his trunks weren’t very large, judging by the big bulge beneath them, it was clear that something else was. The rest of his body was easy on the eyes, too.
Charlie explained that the second interviewer had had to reschedule their meeting, so he had the rest of the afternoon off. Seeing us next to the pool, he’d decided to join us.
I was a little bit uneasy as I hadn’t planned on showing so much skin to my new houseguest; however, I now had proof of what my neighbor had claimed—he was definitely checking me out. I found myself in a bit of a quandary since if I left it would look like I was avoiding him (which I wanted to), and I had to admit now, confronted by his open admiration of me, that I enjoyed his attention. I was desirable for the first time in months, and it felt really good. And since I really had no easy way out of the situation, I decided to remain where I was.
After the three of us chatted for a while, Jessica flipped over onto her stomach and asked Charlie if he would oil her up, something he was eager to do. She played it up, insisting he really rub it in. The harder he rubbed, the louder she moaned, and she kept it up until he was all but openly feeling her up. She then asked him to undo the ties to her top, as she didn’t like tan lines. He rubbed there as well, coming very close to her breasts. That made her moan even louder.
Jessica finally said that was good enough, then suggested he do the same for me. I wasn’t thinking clearly enough to come up with an excuse to turn him down, so I flipped him on my stomach and had him oil me up as well. I certainly didn’t encourage him the way my friend had, but I did enjoy the feel of his hands on my flesh.
After oiling us up, Charlie got into the pool and began swimming. Again I found myself admiring him, idly fantasizing about him doing some naughty things to me. No man had ever had this kind of effect on me before.
After about half an hour or so, Jessica whispered that it was time to turn things up a notch. Before I could talk some sense into her, she flipped over onto her back, now topless, and called out to Charlie. When he noticed her state of undress, he tensed for a moment, but then collected his wits and walked toward us. Jessica somehow sounded completely innocent as she informed him that she needed her front done, too. Charlie looked over at me, as though I’d object, but Jessica was old enough to make decisions on her own and would probably kill me if I tried to stop it, so I said nothing.
I watched as he rubbed the oil into her pert breasts, making her purr. My mind reflexively envisioned him doing that to me, and I suspected my reaction would be identical to my friend’s. I was so envious of her ability to do what she wanted.
Jessica had him stop then and once again suggested he do the same for me. I was shocked. I mean, I wanted him to do it, but to have her openly speak my thoughts out loud? Then again, she knew I was too reserved to do it on my own. I realized it wasn’t proper in the slightest, but Jessica had been right on the money about everything—my mental state, my attraction to Charlie, what I wanted to do—so I allowed her to guide me.
I turned over and put my breasts on display for my guest’s benefit. Charlie, who already had a smile plastered on his face, got an even bigger one. He was all too delighted to squirt the liquid on my chest and begin rubbing it in. My breasts are a good bit larger than my neighbor’s, so he had much more to work with as he massaged my flesh and worked in the oil. As Charlie did that, I noticed the impressive bulge in his shorts continue to get bigger until the head of his cock strained against the front of his trunks. It was very big, and I could see a droplet of precome ooze through the material.
Jessica noticed as well, and said it looked like he had something that needed to be taken care of. She instructed him to come over to her, which he was only too glad to do, then pulled down his trunks. Out sprang a good eight inches of thick cock, by far the biggest I had ever seen in person. Not bothering with another word, Jessica opened her mouth wide and took the large head inside. I just about drooled as I watched her slurp around the head. I figured such a large thing would be too much for her to handle, but she kept working it further and further until she had close to three-quarters of it disappearing down her throat. That answered any question about her being all talk, as there was no way she could pull that off without a lot of practice.
In no time at all, Charlie gasped out that he was going to come. Jessica suddenly pulled his cock from her mouth and aimed it down at her chest, where he released a load so big it really did decorate her tits.
“Nice,” she said, rubbing it in.
After seeing that, I wanted some as well, and there was no denying it. I told Charlie to come over so I could clean him off, and he was only too eager to oblige. I was slobbering all over that huge hunk of manhood in seconds, opting to lick it more than suck it. It twitched in my hand after a few moments and got hard again.
Charlie said he wanted to return the favor. He repositioned us in a 69 with him on top. He pulled my bikini bottoms aside and drove his tongue deep into my pussy. Jessica wasn’t the only one with expert oral skills, and he had me juicing in no time at all. I returned the favor by sucking on his cock as best I could, no easy task with the way that tongue of his worked its magic.
Then Charlie rose up and moved around so we were facing the same direction. It didn’t take a genius to figure out what he wanted to do now, and I wanted it just as much—probably more, actually. I spread my legs in anticipation, and Charlie put his cock right up against my entrance, rubbing it up and down my slit. He got me so wired that I was about to beg him to fuck me. But he saved me the request by lunging forward and making me cry out as that big head and a few inches of his shaft were shoved into my pussy. He paused for a moment, allowing me to adjust to his size and his weight on top of me. Once I got used to how it felt to have that massive thing in me, I started to realize what I was in for.
Despite his tremendous size, Charlie was able to work his cock deeper using a slow, relentless pace. He was stretching me in a way I never imagined, and it felt wonderful as inch after inch of that organ of his made its way inside me. When his pelvis finally rubbed against mine, I could scarcely believe it. Oh God, he felt so good! Then he started moving his hips, and I realized how much better it was about to get.
As Charlie began shuttling his cock back and forth, he groaned loudly, telling me how bad he’d wanted to fuck both of us from the first day he arrived, but never in his wildest dreams had he imagined he’d get the chance to do it. Those words were positively thrilling. Believe me, when some hot young stud lusts after you just as much as a much younger woman, it does wonders for your self-confidence.
As that big thing worked its magic, I felt a massive orgasm building. I hadn’t had one in just about forever, so I wrapped my legs around Charlie’s waist to make sure he wasn’t going anywhere as I begged him to keep fucking me with that big cock of his. He took that plea seriously and began pounding me harder. The sound of his flesh against mine reached my ears then, and the sound made me hotter. No more than a few thrusts later, I came so hard that my eyes actually teared up. I think it might have been the most satisfying orgasm ever, especially after all I’d been through the last few months. He was making me feel like a woman again in every way.
But Charlie wasn’t done yet. He continued fucking me right through that orgasm and started building me up to another one. As he pounded away, Jessica asked me if she hadn’t been right about his fucking me being a great idea. I gasped out that it was the best one she’d ever had. She smirked and said, “Damn right it was.”
Charlie kept at it, making me come one more time before he let loose a load of come that drenched my insides the way his first load had drenched my friend’s chest. It was only with great reluctance that I released my legs from around him after he went limp.
Jessica was quick to take the initiative then, saying she wanted some of what I had just experienced, and she began sucking away on his cock again. He said she was the best cocksucker he had ever met, and he proved he wasn’t just bullshitting her by getting hard again in almost no time at all.
This time, Jessica wasn’t going to be satisfied with a mere blowjob. She had him lay on his back and got on top of him, controlling the tempo as he penetrated her. I noted happily that while she might have had the edge when it came to oral talent, I was able to handle his cock more quickly, though she eventually got it all in and rode him to several orgasms of her own before he let loose a third time.
We all needed a break after that, so we ended up sunbathing in the nude, which was actually quite erotic, enough so that Charlie’s erection made yet another appearance. He suggested we go inside to my bedroom where we’d all be a bit more comfortable then. As we walked to the house, he wrapped an arm around each of our waists.
Once we were in my bedroom, which had the larger bed, Charlie started directing the action. He had us get down on all fours next to each other on the bed. I thought he was going to fuck us, but instead he crouched down and took turns eating us out. Eventually he fingered one of us while eating the other, keeping us both constantly wound up and on edge.
Charlie had us both practically begging for it before he finally stood up, withdrawing both his fingers and his tongue. He then repositioned himself behind me and shoved his cock all the way into my wet pussy with one thrust. I was still loose from that previous fucking, so he was able to give me a much faster fucking than before. I loved it! He took me in a way my husband of 20 years had never managed, and in no time at all I was howling as he once again made me come harder than I’d ever believed I could come.
This time, rather than continuing to fuck me through my climax, Charlie moved over to Jessica and began to fuck her, but at a much slower pace. It wasn’t long before he had her shouting down the walls, too, and once her climax passed, he came back over to me and picked up where he’d left off, quickly making me come again. Then he moved back over to Jessica.
Talk about staying power. I lost track of how many times he made the two of us come, but it was for damn near an hour—probably the best hour of my life, too. But as they say, all good things must end. Charlie was giving it to me harder than ever and making me climax again, but this time he fucked me through it, giving me a second orgasm so quickly that it was like the first one had never ended. After I came, he quickly followed, allowing his sperm to flood me one more time. And then we were done—at least for the moment. All three of us were exhausted, and we collapsed on my bed.
That was only the beginning of something truly fantastic. From that point onward, Jessica and I gave Charlie unlimited access to our pussies. But even with all that sex, Charlie never acted arrogant or treated us like sex objects. On the contrary, he was nicer than ever and had started referring to us as “his girls,” taking great lengths to never play favorites. He took us on individual dates at least once a week, and a couple of times we all went out together on what we jokingly called “double dates.” He spent the night with whoever he went out with, and when it’s all three of us, we ended up in the same bed for a full night of extremely passionate sex.
Now, not only am I a happier woman than I’ve been in years, but I also feel closer to my friend than I have since we met, and she’s admitted to feeling the same way. And to think, sharing a man usually has the opposite effect.
Recently, Charlie got a job and is now making enough to be able to live on his own. But he said he’d be sticking around my place for a while since it’s obvious I still need a man around the house. Jessica and I agree.