Sexploits Ch. 01: Pamela

Throughout high school and college, I resolved to abstain from sex until I found the right girl. This girl didn't necessarily have to be "the one," but at least someone with whom I had developed a trusting relationship leading up to that glorious first time. It didn't have to be "hot" as long as it was meaningful.

I thought I had found that girl when I became good friends with Jessie, the 5'5" brunette with brown eyes, slightly tanned skin and incredible sex appeal. My involvement with Jessie over the past three years is well-documented in my other writings, but back when I was freshly out of college, I never imagined I would fulfill my every depraved fantasy with the girl whom, to this day, I would consider one of my best friends. Back then, after an attempt at a relationship with Jessie failed, I gave in, surrendering the ideal of holding out for someone like Jessie. It didn't have to be "meaningful" as long as it was hot.

Still, I didn't really think I would give in to some kind of hookup, even after things with Jessie fell apart. However, the winter following Jessie's marriage to another man, I spiraled into what I would consider now to be a depression. One night during that trying time, a good friend of mine invited me to midnight bowling with him and some of his friends. One of those friends was a slightly older, petite woman named Pam. Pam would change everything that night, even if it was just one night.

Pam was not the kind of woman I thought would be the first girl with whom I'd go home. She was about seven years older than I, for starters, putting her in her 30s while I still had most of my 20s ahead of me. She also had two kids, though her body would have never indicated such, as her slight, 5'2" frame probably didn't break triple digits in weight. Despite those stats, though, her features were amazing, even under her clothes. Her breasts, undoubtedly aided by her previous childbearing, were large and supple for her frame, practically bursting out of her tight, low-cut, pink top that night, and her ass was perfect and round in her blue jeans. Her face was very pretty as well, complete with bright blue eyes and a mouth that I knew would look good around my cock. Her hair was light brown and reached her shoulders, where it curled out, framing her face nicely.

Going into that night, I would have never entertained even fantasizing about a woman much older than I, but once I started to get to know Pam, I knew I'd be beating off to the thought of her that night - that is, if the stakes hadn't risen like they did. You see, a couple things I learned about Pam right away were that she was very outgoing and exceptionally sexual. Also, for whatever reason, she took an instant liking to me. All of those things came into play to lead to what would be a night I will never forget.

Pam and I hung out at the bowling ally for most of the night, telling each other about ourselves, how we knew the friends we were with that night and occasionally just goofing around. I found out that this night out was kind of a goodbye for Pam, who would be moving out of the area in another month. The kids were sleeping over at schoolmates' houses tonight, allowing Pam at least one more Friday night out with some of her friends.

The twist finally came when Pam asked me if I was a virgin. With nothing of which to be ashamed, in my opinion, I told her I was and confided just a tiny bit to her about my present personal situation. She asked me if I had spending time meeting other girls, which I had not been, but at this point, my buddy played wing man.

"All the time," he said to Pam. "I'm always pulling girls off his junk to get him to hang out with me." I remember those words like they were yesterday, and at least now I don't have to try to hold in my laugh. While my friend's statement was clearly untrue, given that I had just confirmed my virginity, it still set Pam up for her next statement.

"I'd get on his junk if I weren't moving away!" Pam said instantly.

"Well," I said, without really considering the implications of what I was saying, "that's a a whole other month away." Pam, who had been looking at my friend, darted her eyes over to me, a grin creeping across her face.

"That's true," she said, trailing off as she got up to bowl next. The moment ended there, and the night continued on as it had been so far, except for the fact that now I couldn't stop debating in my head if I would really have sex with this woman if I had the chance. Never had I imagined my first time would be with a mom, but she was a dead sexy milf, and any number of guys would be proud to bag her, first time or not. This back-and-forth warred in my mind right up until I was walking Pam to her car at the end of the night out.

We had all driven separately, so our other friends had already parted ways. Pam parked just a few spots down from where I was, so we continued in the same direction until I reached my car, at which point, Pam hugged me goodbye, told me to not be so down on myself and then continued toward her vehicle. I noticed reluctance in her departing from me, which, along with the hug and her parting line, I figured to be a signal. In that moment, I was convinced that I could have sex tonight if I wanted. Maybe it was the fact that it was 2 in the morning and not the time of day for my best judgment, but I finally made up my mind.

"Pam!" I called to her, and she turned around immediately, a smile on her face and her blue eyes staring at me attentively. "Maybe I can follow you to your place?"

Pam's smile grew wider, and she took a few steps toward me. "Yeah," she said. "Yeah, I live right down the street. I have to get up at 7 for work, but what the hell? I'm only there for a couple more weeks. I can stay up a little longer. Who knows when I won't have the kids again, you know? See you soon."

As Pam got into her car, I was rock-hard in seconds despite the fact that it was 20 degrees outside. I hopped in my car and followed Pam just five minutes or so until we pulled into the driveway of a cute ranch house in your typical family-friendly neighborhood. Nothing family-friendly would be going on inside that house tonight, though.

We entered the house into the living room, taking off our shoes and coats once we stepped in and Pam had hit the lights. Throwing her keys onto the coffee table, Pam said, "Don't forget, I do still have to get up early," as she slowly stepped toward me. Impulsively, I lunged at Pam, wrapping my arms around her tight little body and pulling her close to me as I leaned down and kissed her right on those beautiful lips. Pam immediately threw her arms around me and thrust herself against me, practically humping me as we made out in her living room. In that moment, I had never wanted to be inside a woman more in my entire life.

Breaking from the kiss just briefly, I asked where the bedroom was. Her hands still running up and down my back, she said through heaved breaths as strands of hair fell in her face, "Right down the hall." We went back to making out, only now we were shifting toward the hallway while Pam pulled up on my shirt.

We stepped back from each other just slightly so as to more freely head toward the bedroom while also beginning to undress. Pam pulled my shirt off and tossed it on the floor, commenting with a smile that I obviously worked out. Frozen with nerves, I stood there, unable to respond until Pam took my hand and led me to the bedroom.

With only the moonlight reflecting off the snow outside to illuminate the room, Pam held onto my hand until we reached her queen-sized bed, upon which she then sat, her hands on either side of her as she smiled from ear to ear in the dim light. Frozen again, my mind raced with the realization that I was finally going to have sex right here, right now and with this hot milf.

"Don't you want to undress me?" Pam said seductively. Snapping out of my trance, I joined her on the bed and began to kiss her again, this time mustering the nerve to squeeze her breasts, which were delightful, I might add. I may have been a virgin up to that point, but it wasn't the first time I had gotten to second base. I had a couple other sets to which to compare these boobs, and, at the time, they were the finest I had had the pleasure of handling.

After briefly massaging Pam's breasts through her shirt and lowering her onto her back on the bed, I finally pulled up on her top, getting it up over her head and then discarding it disdainfully on the floor. Without a moment's hesitation, Pam reached around her back and unlatched her bra, quickly discarding the garment and allowing the moonlight to dance upon her bare breasts as they gently heaved up and down in preparation for what was about to transpire. Now it was my turn to give the compliments, as I made Pam fully aware of how I admired her topless body. She smiled, thanked me and then asked me if I wanted to lick them.

With no objections, I leaned forward and, while squeezing her right boob with my hand, I licked and sucked on her left nipple, causing the slightly older woman to writhe beneath me. Then I switched my mouth to the other boob, giving it similar treatment while clutching the breast on which I had just had my mouth. Every so often, I would look up at Pam while I played with her boobs, and she grinned with delight whenever she wasn't in the middle of quietly moaning.

Building confidence, I began to kiss down Pam's stomach until I got to her jeans, which I quickly undid and pulled off her short but slender legs, leaving the woman in only her white panties. Needing no instruction, I reached inside the panties and immediately began to explore Pam's slit, which was a new experience for me. I seemed to be doing all right, as Pam squirmed even harder than she did when I had attended to her breasts, and, eventually, I managed to work my finger inside Pam's pussy. Sliding one finger in and out of Pam's love hole, I used my other hand to begin to remove the garment that separated my new friend from total nudity.

Pulling my hand out of the panties, I put both hands on the garment and pulled it down those sexy legs, intentionally leaving it hanging on Pam's right ankle. Pam smirked and kicked it off, her completely naked body now on display for me. Once again in a sort of trance, my eyes scanned every inch of Pam's skin until the older brunette insisted it was my turn to take my pants off.

I pointed out that having been the one to take Pam's pants off, Pam should be the one to take mine off. She consented, and I got out of the bed to stand beside it, next to Pam, who rolled onto her side and reached for the button of my jeans. She quickly and efficiently pushed the pants and my underlying boxer briefs all the way to my ankles, grabbing hold of my engorged cock before I could even step out of the clothes in which I was standing. With a loud moan, I watched on with disbelief as this girl I just met stroked the entire length of my shaft, ensuring it was as hard and long as it could get, just in case it wasn't already.

We were now both naked, and Pam was beating me off, reminding me how I had originally intended to stroke myself tonight to the thought of Pam. Instead, I was experiencing the real thing, and we were only just beginning. After just a minute of her soft, small hand's rubbing the entire length of my shaft, Pam settled her hand on the base, leaned forward and took me in her mouth.

I cursed, complimenting Pam on how well she was sucking my cock as he her head bobbed back and forth. She pulled back for just a moment to tell me, "If you think that's good, just you wait," and then resumed blowing me as she lay on her side on the bed. My hands found their way onto Pam's body, one running through her hair while the other sought out her left breast and squeezed it while the milf continued to rock her head back and forth, polishing my knob expertly. There was definitely a gap in experience between the two of us, I could tell - as if her having two kids wasn't an indicator already. Pam didn't hold it against me. She seemed to honestly enjoy it.

At last, Pam pulled back, released my cock and said, "Do you want to fuck me?" I had never wanted anything more in my life. Scrambling back into bed with my new, beautiful friend, I positioned myself between her legs as she rolled back onto her back, spread her legs and lifted them up past my shoulders. Even in the low light, I could see her juices glistening between her spread legs, indicating that we were both ready to go. In just another moment, I would be saying goodbye to my virginity forever.

With her legs uplifted and spread, Pam reached down with both hands and used her fingers to hold her pussy wide open for me as I pushed my prick against the wet hole. Now all I could think about was hoping that I wouldn't prematurely shoot my load. After all, it was about as excited as I'd ever been. I did just fine, however, and, with Pam's help, I shoved the tip of my cock into the milf's pussy and wrapped my hands around her thighs as I thrust forward, slowly but surely sinking into my lover's body. Pam and I watched on in unison as inch after inch of my phallus disappeared inside Pam as my body joined hers, the first time it had ever joined to anyone's. With a loud grunt and a pleasured moan, I pushed forward one more time until my balls made contact with the lovely woman's taint.

Goodbye, virginity; hello, Pam's pussy. Once I was sheathed inside Pam, I leaned forward, lying down on top of my first lover while her left leg was still caught over my right arm. Her other leg curled around my waist while her hands grabbed my ass and pushed me as deep as possible into her tight, wet cunt. We both moaned in unison and then kissed, forcing me even closer to Pam until my chest pressed against those wonderful tits. Then I lifted my arm to free Pam's leg that had been trapped there, and we were both comfortable and ready to go. Once Pam had both of her thighs pressed against my waist, I began to dive headlong into this intoxicating experience.

With my head on Pam's shoulder and her head buried in my neck, I wrapped my arms underneath her, around her lower back, and began to thrust up into her pussy slowly but hard. Each time I pushed into her tight, petite body, Pam sank her fingernails into my back and moaned. I grunted with immense satisfaction as my whole body was stimulated by the pleasure of driving my cock into this beautiful woman. We made out a little bit as we fucked, but, for the most part, we just clung to each other and enjoyed the feeling of our sex organs' joining.

As I grew more accustomed to the new feelings, I started to thrust into Pam faster and faster, still nailing her hard like the whore I was guessing she was. Pam's cries got higher as my thrusts became quicker and more powerful, and her nails dug deeper into my flesh. The smell of sweat and sex filled the air around us, adding to the indescribable sensations. These odors weren't exactly ones you'd want for a candle or incense, but in this context, they turned me on only more as my rigid prick delved as deep as possible inside Pam's delightful body. That same sweat began to mingle between our bodies that were pressed tightly together as they were joined in the hottest and most intimate way possible.

It didn't take long for me to get the hang of it, not that there was a whole lot to it. I held tightly to the beautiful woman underneath me and steadily pushed my hips up into her, shoving my cock deep into her tight, wet twat each time. Pam writhed and moaned beneath me as she clung to me, begging me to go faster. I did just as she asked, thrusting harder and more quickly until I settled on a pace that was steady and effectively but wouldn't wear me out too quickly. Meanwhile, Pam ground up against me, holding tightly to my shoulders as she met my pumps with thrusts of her own, ensuring that my entire cock was getting treated to her wet vagina.

Our moans got louder and were now joined by the steady smack of my flesh against Pam's. The intensity and passion of the moment far exceeded anything I could describe. I had been anxious going in that the experience wouldn't meet my expectations, and while there had been an initial awkwardness I couldn't avoid, once we were deep in the throes of intercourse, it was everything for which I had hoped. With her sweat-soaked breasts pressed against my chest, Pam called out my name and clawed at my back as she begged me to keep rocking her sexy body hard and deep.

I'd like to exaggerate and say I fucked Pam that night in several different positions, which I really wanted to do. However, the fact of the matter is that it was my first time having sex, so simple did it. I still managed to give that sexy whore the good, stiff pounding she required, holding onto her tightly and managing to pick up my pace even a little more as I nailed her into the mattress beneath us. As my balls slapped against Pam over and over again, at one point she kicked her legs out and cried out, insisting that she was cumming. Whether or not she was faking it, I couldn't honestly tell you, but it still made me happy to think she was climaxing, and I determinedly thrust in and out of her relentlessly as her tight, wet pussy clung to my cock which drilled it hard and deep.

The mattress squeaked beneath us and the bed frame rattled as I pumped in and out of that sexy milf over and over again. I simply held onto Pam as if for dear life while her hands ran up and down my back, her legs alternating between thrashing on either side of me and wrapping around my waist as my balls made contact with her taint again and again. My body was now practically slipping against Pam's sweat-soaked flesh, and I could hear the girl's heaving breaths in my ear as I continued to pound her twat. For being afraid I'd fire off too quickly when we started, I have to say I was proud for lasting as long as I did my first time.

It got pretty noisy in that bedroom for a while as the sounds of my flesh slapping against Pam's, the rattling bed and our cries of pleasure filled the room. At last, with Pam's limbs wrapped tightly around my body, I slowed to a stop inside her wonderful vagina and whispered to Pam that I was ready to cum. In fact, I was barely holding it in.

Pam relaxed her arms and legs, allowing me to pull out, and then pushed her boobs together with her hands and asked me to cum on them. Without a response, I got to my knees and aimed for what I had already made up my mind to aim for. Stroking myself vigorously with the image of this naked, sexy milf babe to aid me in achieving an orgasm, I moaned loudly and pointed my cock directly at that pretty, grinning, unsuspecting face.

I cursed as unimaginable pleasure coursed through my body, forcing myself to keep my eyes open and watch as a thick rope of cum erupted from my cock and blasted Pam right on her left cheek. Immediately, Pam cried out and giggled, her hands coming off her boobs and just helplessly hanging in the air as I fired off a couple more shots at Pam's face before decided to do as she had asked and depositing the rest of my load on those lovely tits. I'd managed to get cum on Pam's lips and right in her left eye before the rest spurted out onto her rack. I had been so turned on for this activity that I certainly had enough cum to go around.

It was now well after 3 am, and I was beyond the point of exhaustion. As soon as I finished my orgasm, I collapsed next to Pam in the bed, who looked at me with her one open eye and grinned as cum trickled down her face and breasts. We were both catching our breath and letting out happy sighs as we came down from, what was for me, anyway, an unforgettable experience.

I got up with Pam just a few hours later, kissed her goodbye and headed home, not jealous of the fact that Pam had to go work an eight-hour day after just four hours of sleep. When I got home, I looked Pam up on social media, and, from there, we did chat a couple times. However, despite that the one time we had hung out ended in hot sex, I never did see her again. I could have inferred that Pam hadn't had a good time, but she did constantly communicate with me online, and I was pretty confident she had had plenty of fun. Having two kids does make it difficult to have nights like the one we had, after all.