I was never what you would call "popular" with the ladies. I was never fighting through throngs of girls. So it wasn't really a surprise when after my 19th birthday I still hadn't ever had a serious girlfriend or lost my virginity.
I was always more into computers than real people anyway, or at least that is what I tried to tell myself. Which leads me to my mom's best friend. They had met while they were in college, and while my mom had settled down and had children Janet had never really lost the rebel fire they had both had in their youth.
A bad marriage and a messy breakup led to Janet staying with us for awhile while she was looking for a place of her own. I pretended to be annoyed at having another person in the house, but secretly I was thrilled, because Janet was fucking hot, well if you are into MILF's.
I never really hoped for anything to happen, maybe catch some glimpses of her in her underwear, maybe "accidently" walk in on her in the shower if I was lucky. I wasn't prepared for her to be my first. It started out with me trying to spy on her. I was pretty sure that I had a good spot to watch her changing clothes from without being caught but I got spooked when she looked in my direction and rushed off back to my room. I thought my heart would explode in my chest when she knocked on my door a few seconds later.
I wasn't sure what to expect, maybe a telling off, maybe some threats, but nothing prepared me for what came next. "I saw you spying on me." she said. "I'm sorry." I said, hanging my head in shame. "I didn't say it was a bad thing did I?" she responded She pulled back her pants, giving me a glimpse of the lacey black panties she was wearing under her jeans.
I felt my heart skip a few beats and my palms immediately got sweaty. "You don't have to spy on me you know." she said "after all I am right. next.
door." her hands slid up her stomach and cupped her breasts as she spoke, sending an unequivocal message as to her intent. I stuttered something incoherent, my brain not quite working properly due in large part to a majority of my blood flow having been directed to lower places. I had watched her with lust in my eyes since I hit puberty, I wasn't entirely convinced that this wasn't some sort of dream.
I was still trying to process what she had said when she closed the distance between us and pressed her lips against mine. The sweet flowery scent of her shampoo and body wash filled my nose, her lips pressed firmly and insistently against mine. I could feel the hunger in her body as she pressed against mine.
A million years of evolutionary instincts took over and my arms slipped around her, pulling her tighter against me. One hand cupped her ass, pulling her hips to me. My cock swelled in my pants and she moaned as she felt my swollen member press against her through our clothing. Her tongue wormed its way inside of my mouth, full of warmth and desire. Our mouths battled with each other, each desperate to gain some sort of leverage over the others. My hands started to get braver, one hand slipping down the back of her pants and cupping her bare ass.
She moaned into my mouth, the sound muffled by our warring tongues. I thrilled at the feeling of her breasts pushing against my chest. This was already as far as I had ever gotten with a girl.
Our bodies separated briefly and I took the chance to slide my hand up between us, pawing at one of her breasts over her clothing.
My cock was straining and begging to be freed. She giggled at my clumsy attempt at feeling her up. In a scarce handful of seconds she shucked her shirt and bra, another few seconds freed her of her pants as well. In mere moments she went from my mom's friend, fully clothed, to a naked goddess standing in front of me with nothing but her modesty and a tiny pair of black lace panties, neither of which covered much.
I am not sure if my jaw literally dropped but I probably did a passable impression of a fish out of water. She giggled again, "you seemed like you were trying to get somewhere, so I figured I would help you out." I gulped and did the sensible thing and kept my mouth shut.
She returned to the circle of my arms, her body radiating heat like an open furnace. What had been a dull ache before was now a desperate desire that surged inside my chest. The part of my brain that made sensible decisions shut down, all that was left was the animal section that wanted to rip off what remained of her clothing and take her, preferably as roughly as possible. I never knew that this part of me had existed, but I wanted to bite her, to scratch her, to mark her as mine.
I grasped at her breasts, now unrestrained by her clothing. "Gentle" she cooed at me in a tone that was both breathy with desire but held hints of reprimand as well, "they are attached you know" she giggled at the last part. Her hand covered mine and pressed softly but firmly against her flesh. "I want to feel your pussy" I moaned into her ear full of eager desire She took my hand and guided it down between her legs, I pushed the thin piece of fabric that covered her crotch out of the way, exposing the soft full lips of her pussy.
Wet heat rolled out from between her legs as I slipped one finger into her tight hole.
She bit her lip and closed her eyes, appearing to enjoy the touch. I forced my index finger deeper inside of her, penetrating deep inside her womanhood. I reached as far inside of her as I could and started to force a second finger inside of her, she moaned at the additional intrusion into her pussy.
I started to slide my fingers in and out of her cunt, feeling the gentle pressure of her muscles on my intruding fingers, I increased in speed slowly, pumping in and out, the moisture of her arousal easing the passage of my fingers. One of her hands shot out and gripped mine around the wrist, freezing my fingers in place inside of her. She made a sort of guttural growling sound in the back of her throat and her body shuddered.
"god damn that felt good" she said smiling. "what happened?" I asked, confused. "I just had an orgasm" she said, her tone indicating that I should have realized that on my own. "Oh I thought women usually threw their head back and screamed when that happened." I said blushing furiously "Only in pornos" she laughed. "Now it's your turn" She dropped to her knees in front of me and started to unzip my jeans. I was worried that my cock was going to pop up and hit her in the face, as much tension as I could feel in it as it strained to free itself.
She made another growling sound as she released my cock from inside of my boxers, sliding on hand along the length of my shaft.
A small bead of precum glistened on the tip and she scooped it up with one finger before sliding it into her mouth. She made a sound of approval as she licked her finger clean. She took my cock in one hand and brought it up to her face. I shuddered involuntarily as she ran her tongue from the base of my cock all the way up to the tip before plunging the entire member into her mouth. She made a slight gagging noise as my cock hit the back of her throat and she seemed a little surprised. "You are bigger than my ex-husband" she supplied noticing my confused reaction I made a noncommittal noise of agreement and she continued.
With rapid bobbing strokes she rose and fell on my cock, each stroke taking the entirety of my cock inside her mouth. I closed my eyes and groaned, the moist heat of her mouth and the deft use of her tongue was like heaven itself. "stop" I said. she looked at me confused.
"I want to fuck you" I said. She smiled and stood up, she slipped out of her panties, leaving them to join the rest of her clothing on my bedroom floor. She sat on the edge of my desk and leaned back, spreading her legs invitingly and giving me an unimpeded view of her body. If my cock had not already been rock hard that would have done it on its own.
For someone in her 40's she had the breasts and body of someone much younger. The absence of children and a strict training regime had kept her in excellent shape. I noticed in that moment that contrary to what I had believed her pussy was not entirely shaven, she kept a small patch of hair decorating the top of her slit. I approached her and stared at her bare body in disbelief. Only 24 hours ago if you had told me that I was going to lose my virginity after all this time I never would have believed you.
I lined the head of my cock up with the opening to her pussy, slipping the head around between the lips of her pussy as I had seen actors in porn do. She groaned softly and scooted towards me slightly, as though eager for me to finally put my cock in her.
When I could take the anticipation no longer I sunk my cock into her, taking the final step into adulthood and leaving my virginity behind me. Her cunt grasped my cock tightly, and had she not been so wet I am not sure I would have been able to force my way inside of her at all. She moaned, more loudly this time, as I slid inside her as far as I could. I started to slide back out again before driving my cock into her forcefully, causing her to slide back on my desk and bump her head against the wall.
"sorry." I said abashed, she smiled in response and urged me to continue.
I started to work my cock around inside of her, leaning over slightly to angle the head of my cock down. She took the chance as I was leaning over and pulled my head down into a passionate kiss.
Again her tongue hungrily searched inside of my mouth. As our kiss broke I saw that her eyes were glazed with lust. I leaned down further and pulled one of her nipples into my mouth, biting it gently and eliciting a squeal surprise from her. With all the care I could manage I pinned her nipple between my front teeth, flicking the end of my tongue back and forth across the sensitive nub. I felt her cunt grip my cock more tightly, the way that it had gripped my fingers not so long ago, and her body shuddered again as another orgasm rocked her.
I could feel the rhythmic contractions as she came. We kissed again and her mouth was cold but no less full of desire. I continued to pound at her pussy, I was surprised that I had been able to last for as long as I already had, especially since this was the first time I had ever fucked someone. I could feel my balls start to tighten and knew that I was going to cum soon. "I'm going to cum" I moaned "pull out!" she commanded.
I obeyed wordlessly and ripped my cock from the warm embrace of her cunt. She again dropped to her knees in front of me taking my cock in both hands and thrusting it into her mouth. She wrapped her tongue around the sensitive head and sucked on it like she was attempting to get a golf ball through a garden hose. This was all that I could endure. An eruption of cum exploded inside of her mouth, coating her tongue and rolling down her throat.
She swallowed and made a satisfied sound as she licked the last of my cum off. "Don't tell my mom." I said, worried now that my common sense had returned with the flow of blood "Yea. I think that would be a bad idea." she said smiling, "after all if she knew we would never be able to do this again, and I bet you will be even better the next time."