Let Tim in on the secret

After about three weeks of this, I made a huge mistake. A few of my friends and I were hanging out and chatting about girls and sex one afternoon (a rare day that I’d agreed to spend some time out of the house, rather than in the naked, sexy company of my hot mom). One of my buddies teased that I was probably a virgin, since none of them knew me to have ever had a steady girlfriend. Being an eighteen-year-old kid, I was just dumb enough, and my pride stung enough, to brag to that I was not only not a virgin, but was in fact fucking a girl on a regular basis this summer. I felt confident in the moment that as long as I left the identity of the “girl” anonymous, there was no harm in a little bragging.

Unfortunately, that kind of claim is not one to go unchallenged among a group of horny teenage boys. None of my friends believed me, and all of them demanded the girl’s identity as proof that she was real, and not a fiction I’d invented to cover for my true virginal status. Since there was no way I could admit my “girlfriend’s” true identity, I wound up humiliated in their eyes, rather than aggrandized.

The worst was my best friend, Tim. He asked me more than once to back off the outrageous claim if I wouldn’t spill about the girl’s identity, and when I wouldn’t do either, as my best friend he felt betrayed and pissed off at my apparently childish behavior. He wouldn’t speak to me for the next week, refusing to return my calls or texts, and passive-aggressively responding with nothing but shrugs or monosyllabic grunts when I tried to confront him at his house during the day when his parents weren’t at home.

Tim’s dad was a long-haul trucker, and only came home for about one long weekend a month—sometimes less. His mom also worked all day, and even some evenings, as a waitress. In fact, she worked at the same restaurant where my own mom used to work as a waitress, which is how we’d originally become playmates as young children, and eventually best friends. What little I’d known about sex before my mom had come from the porn videos Tim’s dad brought home with him in between jobs.

For whatever reason, Tim’s parents weren’t careful at all about hiding their porn in the last couple of years: it would be left lying right out in the open in their bedroom, which never had its door closed. Once or twice, Tim even reported finding a half-watched tape right out on the living room table, or still in the living room player. In the last couple of years, it had grown into quite a sizable collection, too.

Tim and I even had a few favorites among the collection to watch when his parents were gone: three or four videos which feature young-looking guys who got fucked by older women. We liked them because we could imagine that the young guy was ourselves, getting lucky with some sexy older woman. In our all-time favorite scene, a rich couple invite their pool-boy to fuck the wife while the husband watches (and eventually joins in to get a blowjob from his wife). It was a typical sort of scene from those movies, but we liked that one the best because in the end, the pool-boy shoots a huge load of cum all over the middle-aged woman’s face and her huge (fake) boobs, and then she wipes it all up with her fingers and eats it messily. We both always came when we watched that part.

Up until that summer, Tim would often come over to my house not long after my dad and his mom left for work. We’d hang around in my room until my mom finished taking a shower and getting dressed, then she’d make breakfast for us, and afterwards we’d go over to his place to watch porn. This summer, however, I’d never invited him over, since I’d been busy fucking my mom. I was sure the apparent cold shoulder I’d been giving him was the real reason my thoughtless bragging had made him so pissed off at me.

I resolved to patch things up with Tim in grand fashion. I called him up early one morning, almost immediately after my dad left for work, before my mom was even awake. Despite his sullen attitude, I convinced him to come over my place just like old times. Tim showed up after just a few minutes; although we weren’t neighbors, per se, we did live in the same neighborhood. I met him at the door, motioned for him to be quiet, and quickly ushered him up to my room.

Tim was clearly puzzled by my insistence on silence, and demanded an explanation in a whisper, once we were in my room.

“I know I’ve been kind of a jerk lately,” I told Tim, “so I wanna make it up to you. How would you like to see my mom naked?” I asked, with a big, wicked grin.

Tim’s mouth dropped open. He couldn’t believe I was serious at first, but I quickly explained my simple plan: we’d wait until my mom woke up and went into the shower, then spy on her in the bathroom. Tim was afraid we’d get caught, but I explained to him about my experience with the operation, and how my mom’s habits made the procedure virtually discovery-proof.

Tim was surprised to learn that I spied on my own mother in the shower, but he quickly agreed that with a mom as young and hot as mine, it made sense. In fact, Tim’s own mother was only five years older than mine, and was a very pretty blonde herself. When I pointed that out, Tim admitted that he had to agree his own mom was also pretty hot, and although he’d never deliberately spied on her in the shower before, he might give it a try if he thought he saw a good chance.

When we heard the shower running, we put the plan into action. I opened the door and made sure Mom was actually facing away and wouldn’t catch us, then relinquished the view to Tim. Although as I’ve said, the view through our frosted-glass shower doors at home wasn’t very clear, it was enough to know you were looking at a curvy, naked woman. For a virgin like Tim that was enough to be impressive, as I recalled from my own recent virginal days. I thought Tim’s eyes might pop right out of his head, they got so wide.

After a few minutes, I quietly pulled Tim back and closed the door. “She doesn’t take long showers. She might stop and turn soon,” I explained, and led Tim downstairs. I noticed as we walked that he had a stiff hardon tenting the front of his pants.

We sat at the kitchen table, and for the next few minutes, I explained to Tim all about my mom’s ‘special’ pajamas, and the holes under the arms where you could see a glimpse of her bare tits. He was appropriately impressed, yet disbelieving. After I’d explained the potential, and the correct viewing angles, I made an excuse and left Tim in the kitchen while I went upstairs. I quickly warned my mom that Tim was there visiting for breakfast, so that she wouldn’t unthinkingly come downstairs naked and calling out how hungry she was for a taste of my cock, like she had many recent mornings. No sense freaking Tim out too soon—or Mom, for that matter.

I also made an effort to emphasize how Tim was practically one of the family, and that Mom shouldn’t feel the need to get dressed up just because he was here. Knowing that she preferred to be in just pajamas all day if she could—at least, when she wasn’t naked, these days—I hoped that my assurances would be enough to convince her to do that rather than get dressed.

Fortunately, Mom did just that, and as luck would have it—or simple odds, really, since they were her two favorite pairs—she wore one of the sets of pajamas which had the hole under the arm.

As usual when Tim was visiting, Mom fixed us a nice breakfast. As she went about the business of putting the breakfast together and cooking, I helped clue Tim into the opportunities to peek into the gap in Mom’s pajamas. From the renewed tent in his pants—which I could see under the kitchen table from my angle, but thankfully Mom could not from her position walking around the kitchen—I knew that Tim was getting a good show.

After the three of us ate a pancake breakfast, Tim and I went upstairs to my bedroom to chat. For the next ten minutes, after I’d extracted a promise of absolute, strictest secrecy, Tom sat in stunned silence as I told him the story of how I’d fucked my own mom while we were on vacation, and had been fucking her practically non-stop ever since.

At first, of course, he didn’t believe a word of it—although from the renewed tent in his pants, I could tell he found the tale quite a turn-on, nonetheless. As I went on, however, providing more and more details, including the lessons in sexual technique my mom had been providing me from her feminine perspective, I could tell that Tim had started to have doubts. By the end of my story, he was no longer sure one way or the other whether it was true, or all a lie.

Once my tale was complete, Tim began to demand proof: if I really was fucking my mom, he reasoned, I should be able to arrange for more than just seeing her behind a tinted glass door, or through a hole in her shirt. If I was to be believed, he said, I should be able to show him a lot more. In fact, couldn’t I get her to fuck him, too?

I was ****, at first. I reiterated how despite her present willingness, even eagerness, I’d practically had to **** my mother to go along at first. I didn’t want to jeopardize the good thing I had going by introducing a new, unknown element into the mix.

“Yeah? Well, if you don’t get your mom to fuck me,” Tim warned, “I could tell my mom and dad. Hell, I could tell everybody that you two are fucking. You’d be in such big trouble!”

For a moment I was direly angry with my friend for trying to **** me that way, but my rage lasted only second, for two reasons. First, because I remembered that I’d used use same tactics on my mother, and I understood how the powerful **** of frustrated, teenage, virgin lust could drive someone to such measures. Second, because I realized that Tim’s idea would be much better applied to my mom to ensure her compliance than as incentive to motivate my own participation in Tim’s proposal.

I filled Tim in on my plan: he would leave the house, but I would stay and tell my mom that I’d declined his usual invitation to visit his own place, so that my mother and I could spend the day fucking as usual. After five minutes—enough time to get my mom naked and get things started with her—Tim would come back inside quietly, and sneak up to my mom’s bedroom, where he could watch me fuck her. He was to strip naked, and then when I gave him the signal (he would know it when he heard it) he was to come in. Just as when I had used the same tactics on her originally, the combined threat of exposure and the temptation of being already in the middle of the arousing act would ensure that my mother would go along.

The first part of the scheme went exactly as planned: after Tim left, I found my mom, and invited her up to the bedroom. Within seconds, we were both naked, kissing and groping one another’s nude bodies. As we made out, I began to tell my mom all about the hole in her pajamas that I’d exploited for glimpses of her tits for so long. At first she found it amusing, but when I revealed that I’d filled Tim in on the secret, and that he’d been getting a good look at her tits this morning, she was shocked.

She got off the bed and stood up, clearly upset. Undeterred, I wrapped my arms around her despite her attempt to squirm free, and began to knead the soft yet firm flesh of her sexy ass. At that point, I spotted Tim in the open doorway to the bedroom, and I used my firm embrace of my mother to ensure that she stayed facing away from the door. Tim’s eyes widened like saucers when he saw us there naked, and I saw the front of his pants bulge out instantly.

While my friend quietly undressed, I admitted to my mom that I’d told Tim all about fucking her. That really made Mom upset, especially when I told her I’d promised Tim that he could also fuck her. Red-faced and angry, she began to shout at me, but I signaled to Tim, and he quickly strode in, his rigid cock bouncing with his hurried steps. I backed my mom up into him, so that his stiff prick pressed right into her ass, and she abruptly froze and fell silent in shock.

After she recovered, Mom spun around, backing a step away from Tim (a step was all she could manage with me standing right there behind her), and began to yell that there was no way she was fucking the teenage brat.

“If you don’t let me fuck you, Mrs. Miller, I’m gonna tell everybody that you’re fucking Scott,” Tim threatened.

“See, Mom?” I pointed out. “We don’t have a choice. You have to fuck him.”

The fight went out of Mom immediately when she realized how much power over her Tim’s threat really had. Resigned to the situation, she glowered at Tim, who was lightly stroking his stiff cock in anticipation, and asked him wryly what he wanted her to do.