Taking My Son's VirginitybySilkyCherry©
"Ready to go, Wilbur? It's almost 7:50 and our reservations are for 8!" I called out worriedly, tapping my heel impatiently against the wine-colored carpet as I waited for my 20-year-old son to get his derriere downstairs. He was always late for everything. Luckily, his lack of punctuality was one of the very few traits about him that I found annoying.
"I'm coming, Mom! I just need to find my tie!" he called back. I sighed and rolled my eyes, turning to take another look at myself in the mirror to pass the time. My shoulder-length blonde hair looked perfect in its curls; my brown eyes shone behind my glasses; and I'm not ashamed to admit that the little red dress I was wearing made me look more like 25 than 45.
As I admired my own appearance, Wilbur finally scrambled down the stairs with his tie loosely flung around his neck and a look of panic in his eyes.
Putting one hand out to stop him in his tracks, I surveyed him and gave an approving nod before fixing his tie. "You look real darn handsome, hon," I cooed, caressing his tie lightly after I had tightened it around his neck.
A soft blush spread across his pale cheeks, his thick black hair falling into his face. "Thanks, Mama. You look really beautiful too! But you know, you always do, so..."
"Yes, I know. I know," I said with an arrogant smirk on my face. "Now come on. We don't want to be late. Or any later than we already obviously will be, Wilbie!" Slinging my purse over my shoulder, I leaned up to give him a kiss on the lips. He only pecked my mouth back in return.
Now I may have been a little frustrated by his frequent tardiness, but this? This was on a whole other level. You see, Wilbur was more than just my son. He was my boyfriend.
Three months earlier, after I finalized my divorce from my husband, Wilbur took me up to the cabin in the mountains that we used to visit as a family on winter vacations. It was different now that it was just me and him, but it honestly felt much happier and more relaxing than it had ever been when Tony was in the picture.
Anyway, he took me up there with a purpose in mind. On our last night there, he told me that he had been harboring "feelings" for me ever since he was twelve-years-old. That he had been secretly longing for me as soon as he went through puberty, and that his romantic feelings hadn't gone away over the years like he expected them to. Instead, they only intensified until that day, when they finally all came exploding out of him.
Most mothers would probably faint upon hearing such things tumbling out of their little boy's mouth, but not me. I wasn't real darn surprised. All throughout Wilbur's adolescence, I had seen the way he would look at me sometimes. I once found a real voluminous stash of incest porn on his computer. And there were several occasions when my panties would go mysteriously missing for days at a time.
I'll be honest with you...I too indulged in fantasies about him every now and then as he was growing up. As soon as he turned sixteen, he started looking extremely handsome, and I couldn't help but entertain a dirty reverie or two about what it would be like to play a crucial role in his final transformation from boy to man.
But you wouldn't know he had been pining for me all these years by watching how he behaved around me nowadays. We became an item about two weeks after the cabin trip, after I had time to process the information and make the decision that life is too darn short to be spent being "good".
We started dating, and everything had been absolutely wonderful so far. We had the best time together; I couldn't get enough of his company. And you'd think that, being mother and son, the change from platonic to romantic would have created a whole heck of a lot of problems between us, but that hadn't been the case at all. Honestly, it was the most drama-free relationship I ever had in my life.
He treated me like a queen. And I had fallen madly in love with him.
But there was one big problem. Wilbur hadn't exactly touched me the way he should have by now.
I came on to him plenty of times, believe me. I wore my most seductive outfits. I whispered all kinds of suggestive sweet nothings into his ear. I basically threw myself at him, but he just wouldn't cross that line.
He always found a way out of it. Some silly excuse. He got so darn nervous and flustered, and it made me feel completely unattractive, even when I knew objectively that I was anything but.
And yes, I was 45-years-old, but I felt a heck of a lot hornier then than I ever did in the past. And it was because of Wilbur. It was all his fault.
First of all, because--like I already mentioned--I was completely head over heels for him. Sometimes all I had to do was think about him and I'd get a mass of butterflies swarming all around in my stomach.
He was the sweetest, funniest, most talented man I'd ever known. I knew that his entire life as I was raising him, but only recently did I realize that the person I always loved the most could be the person I was also in love with. All it took was one kiss to change my feelings from maternal love to eternal love.
Secondly though, I became intensely attracted to him, physically. He was real darn effeminate, a pretty boy, with high cheekbones and long eyelashes framing his baby blue eyes. Just the type that got me all hot and bothered. I'd never been one to find chiseled chests and veiny biceps all that attractive. It was always the girly boys that got under my skin.
And so, little to Wilbur's knowledge, the reservations I had made for us that night were not for a fancy restaurant like he thought. They were for a cozy bed-and-breakfast on the outskirts of town. I hated that I had to trick my own boyfriend into going to such a place with me, but that was the way it had to be, it seemed. For reasons still unknown to me.
After we got in the car, I rested my hand on his knee and my head on his shoulder as I told him the directions. I loved this kind of physical affection, all physical affection really. I just wanted to be as close to him as possible, and I knew that tonight was the night that we'd become irrevocably close.
"Are you sure we're going the right way, Mama?" he asked eventually, furrowing his eyebrows at the vacant dirt road ahead.
I smirked and nodded, giving his knee a gentle rub. "I'm sure. Just make a left at this next corner, and we'll be there."
Perpetually obedient, Wilbur did just what I said, and even when he parked in front of the bed and breakfast, he gave me the benefit of the doubt. "So the restaurant's...in there...?"
"Well, there is a small restaurant in there, but that's not what we're here for, honey pie," I whispered with hot breath against his ear. I could almost hear his heart beating out of his chest as my little plan dawned on him.
Before he could make up one of his usual preposterous excuses, I slid out of the passenger's seat and sashayed toward the entrance of the B&B, knowing Wilbur would follow me like a puppy. He did.
The inside of the inn was just as beautiful as the photos made it look on its website. Rustic, warm, inviting. A few people were gathered on the mahogany couches in the common area, sharing stories and laughs. The aromas of chicken pot pie and buttery mashed potatoes wafted in through the kitchen. There were perhaps one too many rooster statuettes scattered all over the place, but overall, it was just the kind of place that I knew would make Wilbur feel comfortable.
Me? I tended to go for the real upscale stuff whenever I could manage to. I liked things elaborate, glamorous, and big. But I knew that taking Wilbur to the Ritz-Carlton for our first time would only make him more intimidated and nervous. This countryside B&B was just perfect, and it oozed with romance.
As I checked in and got our key, I watched my son from the corner of my eye. He fidgeted nervously with one of the buttons on his suit jacket, watching the young and old folks mingling over hot cocoa. I could tell he was trying to think of a way out of this, but there was none.
"Come on, sweetie. Our room's ready," I said, linking my fingers through his and turning him away from the people he was watching as if in a trance. He gave me a nervous smile as he snapped of it, taking my hand in return. His palm was damp. I was damp elsewhere.
We headed up the stairwell together, and I was surprised to find that our room was rather big for this size of a B&B. The bed looked welcoming, and there was a fireplace across from it. I set it blazing furiously but roaring gently as Wilbur took off his jacket and placed it on one of the dresser-drawers.
When he started working on his tie, I strutted up to him and ran my fingers down it myself. "Let me help you with that again," I insisted, looking up at him with my usual devious grin, loosening it slowly and soon letting it join his jacket in the discarded pile of clothing items which was soon to become a mound.
After unbuttoning his crisp white shirt, I pushed him down on the bed and slid atop him, not wanting to waste any time. I nipped at his neck, sucking sweetly on his collarbone. He closed his eyes and bit his lip, obviously resisting a moan. His skin tasted so nice against my tongue. I could only imagine what other parts of him might taste like.
After giving his neck some attention, I trailed the most feathery-light kisses all the way down his pale bare chest. Already, this was the farthest we had ever gone, and the night had just barely begun.
"M-mama..." he whispered, hesitantly placing his hands on my hips and soon feeling up the hourglass curves of my waist.
"Yes, honey?" I asked in between kisses, looking up at him when I reached the top of his pants.
"It feels so good, but--"
"But what?" I frowned, sitting upright atop him. "What is it, Wilbur? Are you not attracted to me? You pined for me for years, but now that you got me, you don't want me anymore; is that it?"
Wilbur shook his head quickly as his eyes grew wide. "No! No, not at all!"
"Then what? Because I can't rightly wrap my head around it anymore. I've tried everything a woman can try, and you're never interested. I don't know what other conclusion to come to except...I must not be as beautiful as I think."
"God, Mom, you're even more beautiful than you think. That's not what this is about."
Upon hearing that compliment, some of my anger started to wash away, transforming into confusion and just plain ole sadness. I looked away from him, feeling my eyes sting. My voice dropped, cracked. "Then why is it that I want you...so, so darn bad...worse than you even know...and you'd do anything, you'd say anything, to keep me from having you?"
At this, Wilbur sat upright against the bed and looked at me with big, worry-filled eyes. "Mama..." he started, brushing some hair out of my eyes tenderly. "I want you too. I want you so much that it hurts sometimes. It's been that way for years, for almost as long as I can remember. But I'm just so scared that once I finally have you..."
"...That it won't live up to the fantasy," I whispered, understanding. "That I'll disappoint you."
"What?! No. That I'll disappoint you!" He groaned, clearly annoyed that everything I was saying seemed to be the exact opposite of what he was trying to tell me. "Look, all my life, I've just wanted to impress you and make you proud, and...what if I'm no good at this, and it's like...you're like this perfect goddess of a woman, and if I can't measure up to that...it's just..."
"Shhh, shhh, sweetie," I interrupted, caressing his cheek, usually pale but now the color of a bright red rose. He looked down and sighed. "I'm sure you're good at this. Heck, I'm sure you're fabulous at this!"
"Mom, I'm..." After a pause, he finally looked back up at me, shame in his eyes. "I've never even done this before, so how could I be good at it?"
A deafening silence fell over the room. I could suddenly hear the roar of the fireplace much louder and even the chirps of a few crickets outside. "You...what? But...wait...no, no, Wilbur, what about Mia? And Briony? I thought..."
Wilbur shook his head. "I never did it with either of them. I was kind of...waiting for you. Which is ironic because now I wish I had done it with them for practice, to prepare myself to really know how to please you."
"You were waiting for me?" I asked, to which Wilbur nodded sheepishly, his blush darkening. After a few moments, I smirked and pressed my chest against his. "That is such a turn on."
"Mmhm. Honey, I don't care that you're a virgin. In fact, I'm glad you are. I had been pretty darn disappointed when you first started seeing Mia. I thought I missed my chance to take my baby boy's innocence," I cooed, wrapping my arms around his neck.
"W-what? You mean..." he began, but I cut him off by pressing my lips against his. We closed our eyes in unison and tangled our tongues together as if our lives depended on it. In his kiss, I could feel that he was finally giving in to the passion that had been burning between us for years, never allowed to fully surface.
His body shivered as I moaned into the kiss, but he finally made a move by reaching for the zipper at the back of my dress and pulling it all the way down in one smooth, quick move. I then took my own turn, unzipping Wilbur's pants and pulling them off, exposing the bulge in his boxers.
He wasn't rock hard yet, but I knew he'd get there soon. Just seeing the beginnings of my son's full potential was quite enough to get my heart pounding against my rib cage.
A rib cage that was soon visible to Wilbur as soon as I wriggled out of that red dress and tossed it to the floor. He stared at my pink lace bra, half-nervously and half-excitedly. It was the first time he would ever be seeing his mama's breasts in this context, real darn different from his years of innocently breast-feeding from them.
"Can I...can I see...?" he asked timidly, reaching behind me and poising his hands over the hook of the bra. I nodded softly, sitting up straighter, ready to present myself to him.
And yes, there was a part of me that was nervous as well, wondering if my breasts would look saggy and old to him. But they were on the small side, a solid B cup, so I was fairly confident that they had remained perkier than some of my fellow 40-something D cuppers.
With shaky hands, he unhooked the bra and removed it from my chest. I took a deep breath to make them stick out nicely for his viewing pleasure. His eyes widened to three times their regular size as he stared, his mouth hanging open. He remained frozen like that for a good few seconds, making me feel a little insecure. "Are they okay, honey?"
"Oh, my God..." is all he replied with before suddenly pinning me down on the bed and gliding his tongue over my left nipple. A sharp gasp left my mouth, and it was now my eyes' turn to expand.
"W-Wilbur...oh, my..." I squeaked. He couldn't reply, his mouth occupied with my hardening nipple. Another perk to having small breasts: they were extraordinarily sensitive.
With every lick and suck he gave my tender breast, I felt my whole body tense up with pleasure. He went at both breasts with vigor, his eyes closed tightly as he practically devoured them. Maybe this wasn't so different from breast-feeding after all.
After he freed himself from the strain of his boxers, I looked down and watched his erection grow with every taste of my breasts he got. It didn't take long before his cock was standing at full height. My pussy had remained very tight over the years due to a frustrating lack of sex in my marriage and my equally-frustrating ethics preventing me from cheating, so Wilbur's huge cock almost looked a little too big for me. Almost.
After he got his fill of my breasts, he kissed in between them, trailing down my chest and my stomach with his soft lips just as I had done to him. He was a quick learner. As he did so, he reached down and slipped a finger inside my panties.
My body clearly didn't know that the man I was ready to ravish was my own flesh and blood; it knew no societal norms or moral standards. Instead, it had prepared me incredibly well for the event: my opening was slick with wetness and tense with anticipation.
Plunging his finger inside me, breaking the wall of lubrication, he gasped in surprise. "Oh, my God...Mama, you're so wet."
"You don't have to tell me that. I'm painfully aware." I snickered.
"D-does that mean you...um...are you r-ready or...?" he asked, all the while absentmindedly running his thumb gently over my clit. I don't think he even knew what he was doing, but it made it hard to think straight.
"Mmmm...mmhm," I finally managed to say, ready for anything, wanting everything. He hesitated for a few seconds but eventually pulled his magic fingers out of me, slid my panties off down my long legs, and positioned himself awkwardly on top of me.
I grabbed his hips and pulled him toward me. "Okay, sweetie. Just like that," I cooed as he slowly entered me. A wave of relief rushed over my body, my pussy expanding, welcoming him inside inch by inch.
"Oh, my God. Oh, my God," he moaned. It was becoming his trademark statement.
"That's it. Just like that. Just like that." I left my hands on his hips as he started thrusting in and out, slowly and clumsily at first. I leaned up to kiss him on the mouth encouragingly, and it worked. He kissed me back hungrily and sped up his thrusts, getting into a good, hard rhythm.
Now this is what I wanted. I wanted my shy, effeminate little boy to fuck me like a man. The harder and faster he went, the wetter I got and the louder my moans became. "Wilbur...oh, you're doing so good, baby. You're making your mama feel so good," I cried out, clutching the bed sheets as tightly as my eyes were shut.
"It feels so good, Mama," he whimpered. "Oh, God, I love you, Mama."
"I love you too, Wilb--oh, sweet Jesus!" Just when I thought things had settled into a steady rhythm, Wilbur assaulted my slippery slit by shoving his entire cock into it. There had to be at least nine, maybe ten, inches of cock inside me, as deep as he could go. It was the biggest I ever had before, and it hurt like hell. I screamed and he immediately looked distressed.
"Mom, are you okay?! Do you want me to pull out?"
I shook my head and wrapped my arms around his back, making sure he stayed all the way inside me. It was the best darn pain I'd ever felt. "I'm fine. I was just surprised; that's all."
Skepticism was written on his face, and his thrusts became gentler as he continued plunging deep inside me. He grabbed my hips and lifted me off the bed slightly, allowing him even deeper access. The pain, turning to pleasure as I got used to the feeling of him filling me up so completely, soon become ecstasy when he accidentally found my G-spot. I screamed once again, but this time he could tell it was a scream of joy.
"You like that? Right there?" he asked, smirking a little. He hit the spot again and then pulled back for a few long seconds, teasing me mercilessly.
"Wilbur, stop it. Fuck me. That spot. Again. Hard. Please." Words had almost lost all meaning to me.
But Wilbur was clearly enjoying this moment of power over me. It was rare, and I suppose I should have expected him to milk it. "Why should I?"
"Because I'm your mama and you have to do what your mama says!" I was so close to my orgasm and I needed just one more pounding against my special spot to send me over the edge.
"Good point." He let out a small laugh and then obeyed my demands, pushing himself inside me again, hammering my G-spot not once, not twice, but three times in perfect succession until we both came, hard and loud.
My body shook like an earthquake as his warm juices mixed with mine, tension leaving me from head to toe in waves of heavenly release. We both tried to catch our breath, and the sounds of us gasping for much-needed air completely drowned out the roar of the fireplace and the crickets outside. It was just me, him, and post-coital bliss.