Serena: My Best Friend's Mom

I was 18 and it was the summer of 1981. We used to go over to Darrin's house, three or four of us, and play games like Statis-Pro basketball, Dungeons and Dragons, Monopoly, for hours and hours. When we'd been nerdy enough, we'd go out and play baseball, you know, hit grounders until you were sweaty, then go to the store for some Rondo soda and buy some baseball cards. It was a good time.

One of the distractions that summer was, as always, Darrin's mom, Serena. She was a single mom who ran her own business out of the house, so she was around a lot. She gave off a quiet but steady sexual energy which was never made explicit -- she never said anything overtly flirtatious or touched us inappropriately. Still, being a perpetually horny teen, I read come-on's into everything she said and did. When she said, "Want some cookies, Terrence?" I heard "You have a cute butt, Terrence." But I tried not to do anything stupid.

Darrin was my best friend at the time, a sweet shy kid who seemed proud but embarrassed by his sexy mom. Serena was sort of a New Age product of the Seventies. Her walls were decorated with African masks and she was always "working on her self." A tall brunette, she had freckles on her chest, just above her surprisingly large (for her body type) breasts. They were pendulous, and I often caught glimpses of them because she wore bathrobes a lot and I frequently slept over at Darrin's house. I slept on the floor in his room and we'd leave the door partly open. I'd see her walk back and forth between her room and the kitchen, the robe's belt loosely tied. It took all my willpower not to go out there and try and see more, but I knew she wouldn't go for that.

One time I did get to see her naked, though – and not just a glimpse. Ron and I were over at Darrin's playing some game in his room when Serena ducked her head in the door. She had a robe on and a towel over her shoulder, although it was the middle of a hot weekend afternoon.

"Can you boys move into the living room?," she said. She said it nicely, but it was clearly an order of sorts. "Thanks," she said, without waiting for an answer, and then disappeared.

As we gathered up our stuff – dice, game board, etc. -- I asked Darrin why we had to move. He blushed and turned away.

"She wants to sunbathe," he said. He looked unconsciously at his windows, which overlooked the backyard and its wooden deck. Ah, I thought. Now's my chance! Thinking quick, I surreptitiously "dropped" a couple pieces I needed to play, and moved into the living room.

After we settled into the living room and played a few rounds – I think we were playing a baseball game -- I suddenly "noticed" I was missing something. "I've gotta get my pencil, hold on," I announced, hopping up and moving down the hall before Darrin could protest.

I had an idea that the reason we were moved by Serena was because she wanted to sunbathe nude, or at least topless, but I was absolutely stunned by what I saw. Rushing straight to the window, I looked down to see something amazing: Serena, buck naked, laying facedown on a towel on the deck, her legs spread apart and her pussy actually glistening in the bright sun. I was so turned on, my legs started shaking and my cock hardened instantly.

I should probably mention here that I was a virgin at the time and never actually seen a real woman naked, despite being pretty familiar with the human form through my hefty collection of shoplifted porn. Seeing Serena like this, ass up and covered in tanning oil, was to a teenage boy like finding a nugget of solid gold in your tomato garden.

Serena stirred and I pressed myself against the wall, out of sight. Breathing heavy and frightened that Darrin would come back to his room, I waited before peeking carefully out again. Serena was now sprawled on her back, with a washcloth over her eyes which protected her from the sun -- and from seeing her peeping tom.

She had an all-over tan, a bush of light-brown pubic hair and those big, beautiful breasts spreading out on each side of her chest. What was again amazing, though, was how clearly I could make out her pussy lips. Whether because she had but suntan lotion on them or she was wet down there from some dirty thoughts, a sheen of moisture made them stand out, beckoning me like some kind of Star Wars tractor beam.

Transfixed, I could have stood there for hours, but Darrin snapped me out of it. "Did you find it?" he called out, with irritation from the living room. I grabbed the pencil off the floor and scurried out, my cock literally pounding against my jeans zipper, maddeningly teased.

I repeated this maneuver a couple more times. When Ron picked up on why I was going back there – he saw me forced to readjust my straining member everytime I folded myself down to the coffee table we were using to play on – he suddenly announced he'd forgotten something in the back, too, darting off before Darrin could challenge him.

Darrin, of course, know his mother sunbathed nude. When Ron came back, grinning stupidly, he blushed again. "Let's just PLAY, you guys."

Not wanting to upset him, Ron and I buckled down and played the game, trying to focus – even though the outcome seemed irrelevant when there was a hot naked lady lying out back, looking like she was just dying to be fucked. This went on for about 45 minutes. I got one more look at Serena by saying I had to pee, then darting in for quick peek under the cover of the toilet flushing. She had turned onto her side, to read a book, but was still naked.

Then, a miracle: The phone rang -- it was Darrin's grandmother down the block, asking if he would run to the store for her. He reluctantly left, giving us a last suspicious look. Ron and I continued to play, desultorily, since we weren't prepared to admit to each other what we'd been doing in Darrin's room.

But I couldn't resist; my other brain was in charge. I "remembered" yet another item I'd left in Darrin's room. Back at the window, Serena looked better than ever. She'd flipped back onto her belly and I was now looking at a well-defined ass and that oh-so-inviting vagina. Her face was turned to one side, eyes closed. Involuntarily, I started to rub my cock through my jeans, until its head peeked out the top, nearly reaching my belly button.

"What are you doing?" It was Ron, playing dumb. I stopped rubbing, frozen with embarrassment. Ron came over to the window and looked. "I don't blame you," he said, as he started rubbing himself. Serena, oblivious to the energies she'd set in motion, lifted her knee up parallel to her hip, giving us an even better view of her damp cave, the lips stretching apart.

Ron and I were now both squeezing our cocks through our jeans, squirming with sexual frustration. But we didn't say anything, just watching silently, like we were under some magic spell. I don't know how long this went on – five, ten, maybe 15 minutes. It seemed Serena might be asleep.

Finally, Ron cracked. "Just going to take it out for a second," he murmured. Fumbling quickly, he unbuttoned his Levi's top button, unzipped, and pulled out a thick, weighty, circumcised penis that was twitching lazily, pointing straight out from Ron's lean stomach.

Wow. I was stunned. In its own way, seeing that was as amazing as seeing Serena – I had never seen a hard cock in person before, and now here was one just an arm's length away. I stared unabashedly, before dragging my eyes back to gaze at Serena.

Making sure not to make eye contact with Ron while I did it, I slowly unzipped my pants and withdrew my own hard tool. More slender and long than Ron's, mine pointed up straight at the ceiling, its eyehole flared and head read as a beet. Ron looked it over with a glazed stare, his mouth gently agape.

Seeing that we were now into a new realm where the old rules didn't apply, we shucked pretense and pushed our pants and jockey-style underwear down to our ankles and set up a steady rhythm of stroking. I knew where I'd go if Serena looked up into the window, but in hindsight Ron had nowhere to go in such an emergency, unless he just hit the deck hard – which might have been dangerous in his condition!

As I've said, it was a hot day, and it felt wonderful to have some air on my balls and thighs. Ron and I were now stroking in earnest, having unconsciously settled on the same steady firm syncopation. We stared at Serena like our eyes might burn a hole through her bronze body, alternately with increasingly less abashed glances at our stroke-mate's pulsing member.

At this remove, I wonder idly if we would have let ourselves come if nothing else had happened. That might have been a line – intimacy? – that even our sex-crazed state we might not have crossed. If Darren had turned the know on the front-door, if Serena had made a move to turn over, if the phone had rang – we would have just shoved our still rock-hard pricks into our pants and shuffled back into reality as quickly as possible.

But that is all moot speculation. In the event, Serena, apparently not asleep but rather fantasizing about who-knows-what sexual adventure, suddenly did what neither Ron or I probably had the imagination to even plead with God for: Sliding her right arm from up above her head, she snaked it down under her upthrust thigh and began slowly rubbing her pussy.

"Ohmigawd," Ron exhaled. I could only nod dumbly. There was definitely some strange magic afoot this day. Our stroking almost instantly became faster, more insistent, our hands fairly flying up and down our poles.

Serena's hand stopped moving. Tentatively, slowly, she eased her middle finger in between her pussy lips, which looked more slippery than a mango. Pushing down her left leg, but leaving them spread about two-feet at the knee, she brought her other arm down to help. I think she was playing with her clit with the left hand, while the right rested on top and now was inserting two, and then even three, fingers into her soppy cunt.

Ron couldn't take it. With no more warning than a soft moan, a thick stream of cum shot out of his cock, hitting the window and slowly sliding down the glass. I watched in shameless awe as a second and third shot gushed out over his vise-gripped hand, and then more cum just flowed lazily out the tip, like a little kid's ice cream cone on a hot day.

This was too much for me, and I could feel my own seed rising as I stroked frantically, like a boy trying to rip his own penis off! Ron watched expectantly, still slowly stroking his slick dick as it continued to ooze.

Then we heard the key in the door. Shit. Darrin was back and probably wouldn't be very happy to find us clutching our cum-dripping dipsticks as we stared at his masturbating mother and her plump and naked ass. But I was beyond the point of no return and couldn't stop. The first shot of the sticky stuff shot out onto some paper's on Darrin's desk – his homework, as it would turn out! – and then I pointed the geyser away, hitting the same window as Ron, our come mingling on the pane.

Luckily, there was a box of tissue in Darrin's room. Holding my cock tight, I reached down for a sheet and held it over the tip, before allowing the successive gouts of come up and out my body. The tissue was soaked instantly, though, and tore, leaving cum to run down along my urethra and the pulsing veins of my shaft.

The rest is a blur. Thankfully, Darren had taken his mom's own shopping list and was unpacking some ice cream and other perishables before coming back – giving us enough time to hurridly wipe the smeared cum off the window, Darrin's desk, the floor, our cocks and our pants, as best we could. Let's just say that we got it to wear it didn't look like an orgy had just ended but a detective wouldn't have had much trouble finding some clues as to what happened.

Our cocks still oozing cum, we jammed them stiffly back our jeans, took one last look at the room and each other – I pointed wordlessly to a drop of cum on Ron's alligator shirt, which he wiped off – and then darted out to the living room. Flushed, Ron and I returned to our game as if nothing had ever happened. Soon after we heard Serena, apparently satiated, come up the steps from outside and retire to her room.

Ron and I never mentioned that escapade to each other, although I'm sure he, like myself, used it as fodder for many a jack-off session. I'm also pretty sure Darrin suspected foul play, but he was too embarrassed to bring it up. Very soon after he returned from the store, Ron and I made up excuses of why we had better be getting home and Darrin seemed relieved to see us go.

******

My next erotic encounter with Serena took place some months later during one of my many "sleep-overs" at Darrin's house – for a year or two, I practically lived at his house, as he was my best friend and he lived a lot closer to our school.

That night, as I often did, I kept Darrin up late pestering him to engage in yet another conversation about sex. Even for a teen boy, I was apparently more obsessed than most! Not that he wasn't interested, but I think he just felt uncomfortable with the homoerotic undertones of talking about it with me while we both lay nearly naked under our blankets. Lying on the floor in his small room, I was only about a foot away from him.

For myself, the eroticism of Serena wandering around the house in her robe, as usual, mingled effortlessly with the exhibitionist thrill I felt provoking Darrin. Steering the talk, not very subtly, to penis size, I mentioned that I had read in The Book of Lists about a Mongol king who supposedly had an 18-inch shlong. Trying to imagine what that would look like, I moved the blanket off me to expose my extremely excited cock in the light of the doorway we left open to read comic books by. "If this is 8 inches, then his thing must have been this long! Can you imagine!"

Now, I should say here that while people routinely lie about their penis size, especially when they relay their erotic adventures, this story is true and mine is actually decently big. Not huge, mammoth or gargantuan, but above average – 7 inches on the nose, to be exact. (You didn't think I could resist exaggerating a little with Darrin, did you? If he wanted to get out ruler and double-check my math, he was more than welcome too!) It's a handsome fellow, too, if I may say so myself, lean and graceful, with a certain proportion and good, even coloring. Furthermore, at the time this all happened, I had not yet filled out, making mine look even bigger when set against my six-foot, 145 pound frame. As my first real girlfriend would later say excitedly – "You're all cock!"

Yes, we men sure do love our cocks, and never more than at age 18! Probably that's one reason I was so quick to whip it out for Darrin's viewing pleasure – it was just plain showing off. In fact, on previous nights at Darrin's I had frequently purposefully thrown off the blanket and, pretending to be asleep, lain in such a way that Serena might see me lying there, cock engorged, on one of her nightly trips to the bathroom or kitchen, through the door we left ajar. And if Darrin should wake up and see me like that? All the better.

In any case, big or not, whipping out my cock certainly made an impression on Darrin. He actually yelped at the sight of my swollen, throbbing member. Feeling devilish, I made it jump a couple of times. It was fairly dark in the room, with the only light coming from the moon and the hallway light, but there was enough to get a good look at it.

"Come on! What are you doing?!" Darrin complained. Still, he couldn't take his eyes off my stick as it continued to bob and weave like a punch-drunk fighter. I babbled on about this infamous royal Mongol prick, as if showing your erect penis to a friend was as normal as playing a video game or shooting some hoops. Darrin looked like a man unwillingly hypnotized by a dancing cobra, not sure if it is beautiful or deadly. When I finally let it flop back onto my stomach – the tip comes just to my belly button – he snapped out of his trance.

"We GOTTA go to sleep," he said, flopping over so he faced the wall. "I've got a test first period!"

Well, I didn't – and I was wide awake and horny as a proverbial goat. I stroked my cock a few times, still lying without a blanket. I listened for Serena, but heard nothing; she must have gone to sleep.

Getting up, I pulled on my jeans without bothering with the underwear and went out into the hallway. It was a warm night, and I didn't need a shirt, and anyway, I couldn't seen where I'd thrown it in the dim room. I headed for the living room, where I knew there was a basket of sexy magazines I'd been unable to check out at my leisure.

See, Serena was apparently trying to be a liberated woman, and so she had a subscription to a magazine of that era called Viva. For some reason, either because she was clueless as to what puberty was doing to her son, or because she liked to tease us, she kept them right out in the open. I had been able to get some furtive glances in here and there, but had never been able to just read them cover-to-cover, cock in hand.

(Viva, for those too young to remember, was a soft-core sex magazine for women. It had erotic stories, sexy "couple" pictorials and the like. It wasn't Penthouse, but I was at a stage where the National Geographics my grandmother sent me had pages stuck together, so for me Viva was high-grade stuff.)

They had this nice plush rug in there and I lay on it excitedly with a clutch of magazines. At first, I didn't intend to masturbate right there -- it seemed too dangerous, what with Serena being something of an insomniac. One thing led to another, however, as these things are wont, and before I knew it, my jeans were down to my thighs and I was stroking away slowly but firmly over some very hot letters to the editor.

I must have been pretty engrossed, in fact, because when I finally heard the wooden floor creak and looked up, Serena was standing in the doorway -- and it looked like she'd been there for some time. My hand froze, half-way up my cock. I dared not move, or even breath.

Serena was wearing a black terrycloth robe, loosely tied, and I could see the fulsome curve of her left breast almost to the nipple. She leaned against the doorway, her feet crossed, her long brown hair tousled from sleep.

"Don't stop," she said, her voice hoarse with excitement.

I was terrified, though, and didn't budge. Remember, I had no real experience with the opposite sex, other than a few make-out sessions where I hadn't got past first base. My adrenaline, already up while I was jerking-off, was surging through my body. I'm lucky I didn't just shoot off the floor and fly out the room's big plate-glass window, my fight-or-flight system was so engaged!

Calm and langorous where I was shaking and rigid, Serena untied the belt on her robe, letting it fall open. Then she put her hand to her pussy, cupping it gently.

"Really, honey," she whispered. "Please don't stop."

Something in her voice was both mesmerizing and soothing. I took in a deep breath and relaxed my shoulders. I dropped the magazine and stared at Serena as she began to finger herself. Slowly, tentatively, I began anew to stroke myself.

Serena moved one hand to her distinctively large aureola -- the size of a silver dollar pancake -- and pinched her nipple between two fingers. Her other hand went to her dirty blond crotch, as she began tracing the curvy, glistening petals of her crack. She never took her eyes off me.

As I stroked faster -- not too fast, damn it, I thought to myself -- she dipped first one, then two fingers into her honeypot, arching up onto her tiptoes and moaning deeply. I couldn't believe what I was seeing. As she picked up the pace, thrusting her fingers in and bringing her other hand down to massage her clit, I realized I couldn't stop the train and might as well enjoy it.