She drove me the four miles to her friend’s house, introduced me to Lisa, who I’d only met a few times before, and promised to bring some dinner over for her when she came by to pick me up that evening.
I remembered Lisa from the occasional visits she’d made to our house and recalled that she was one of Mom’s more tolerable friends. I guessed that she was in her early forties, tall-ish, a little soft in the middle with a decent chest, nice, smiling, face and dark brown hair that was cut neatly in a short style that suited her face. Lisa had bright eyes and a voice that was surprisingly high-pitched for her size.
“It’s so nice of you to give up your day to help me,” she gushed. “My son is on vacation in Florida and I got divorced a few years ago, so I’m so glad you could step in at the last moment. Another week and you’d be back at college, or so your Mom said.”
I nodded and stifled a yawn. I looked around the room at the endless line of unpacked boxes. “What do we need to get done?” I sucked up the situation and tried to put a brave face on it.
Lisa explained that she had a system for unpacking. She was looking at each box, determining what needed to be unpacked immediately and what she could put away for another day. Once she had done all of the marking of the boxes, I could carry the appropriate ones to her spare room, but could I please put together her dismantled beds in the bedrooms for her first?
Thankfully she had some decent tools and I had a good idea how the reconstruction should go because there was no instructions. I managed to get both of the beds built and went back to see how she was getting on with sorting out the boxes. Lisa explained that she’d color coded the boxes by room and could I move them for her now. Before I started she offered me a soda from the fridge and said that she was going to drive to a local home improvement store to pick up a few items she needed. She would get something for lunch while she was out and bring it back for us.
When Lisa left I set about moving the boxes to the rooms she’d designated. I stacked them up as best I could to save her space and hopefully still see the contents when she got around to unpacking. Some lace caught my eye as I moved a box of clothes into her bedroom. When I set the box down I opened the cardboard flaps and looked in. A large pile of underwear was under a couple of sweaters.
Unable to restrain myself, I pulled out a pair of white panties with lacy edges. They looked a lot sexier than I’d imagined Lisa would wear and I delved into the box again. When I pulled on the strap of a black bra something came out of the box with the bra and fell to the floor. I looked down and saw a large pink vibrating dildo.
I smiled and picked up the cock shaped dildo. I figured it was about eight inches, definitely bigger than my cock. Back then I’d never handled a sex toy before and it surprised me that it felt softer than I’d expected. Obviously worried about being discovered discovering her secret, and possibly conscious that I was holding a cock, I quickly returned it and the underwear to the box, hoping that I’d arranged things pretty much the way they were.
I finished moving all of the boxes in less than an hour and got another drink from the kitchen. Lisa’s TV wasn’t hooked up yet so I didn’t really know what to do with myself until she returned. I sat on her sofa and stretched out. I probably yawned a few times before I fell asleep.
I was dreaming about a hot girl from college. We were on a beach somewhere and her hands were running all over my shirt, occasionally teasing me by running her fingers across the bulge in my shorts. It was a familiar dream as I’d had my eye on the girl for all of the last semester. I was just lying there on the sand, enjoying her hands as they moved, watching her face smile down at me and feeling her fingers inch inside my shirt.
When I woke Lisa was back, sitting next to me on the sofa with her hand gently resting on my chest. Realizing that I’d been asleep, I sat up quickly and her hand fell away. There was a feint look of shock on her face and it dawned on me that some elements of my dream might have been more real than I imagined.
“I’m… I’m sorry,” Lisa stuttered slightly, adding to her shocked reaction. “I was… just making sure you were comfortable.”
I must have looked skeptical of her explanation, because she suddenly looked worried. “You don’t believe me, do you?”
Lisa was still sitting on the edge of the sofa. As I pieced things together I was reasonably sure that she’d been rubbing my chest while I was sleep, but wasn’t certain about anything. “I don’t know. I was dreaming… were you touching me?”
She looked a little flushed now but maybe something in my tone was nonthreatening because she admitted, “Yes, I was.” Lisa looked further down my body and my eyes followed her to the bulge on my jeans – my normal waking state. “It was hard to resist, you looked so… hot.”
I shuffled on the sofa a little, trying to minimize the bulge, but losing the battle. “I didn’t touch you there.” She was defensive now, then demure. “I wanted to, but… I didn’t want to wake you.”
It was one of those moments that you look back on later and realize things could have been so different…. there I was with one of my mother’s friends, her admitting that she wanted to grope me, and me not really knowing what to say. Thankfully, I said the right thing. “Sorry I fell asleep. I was so tired. Hope you don’t mind. And…” I looked down, “sorry about that.”
Lisa lightened a little and her hand came to rest on my arm. “It’s okay. I know how you young boys are. It’s only to be expected that you wake up like that.”
“Well, it’s a bit embarrassing.” I tried to look bashful, even though I knew she was the one who should be ashamed.
“No, no, no.” Her hand rubbed the top of my arm. “You shouldn’t be ashamed. It certainly looks like you have nothing to be ashamed of. Not if that’s anything to go by.” She motioned with her head towards my crotch.
Lisa’s hand moved to my chest as she looked down my body, back to the bulge. She made a big sigh and asked, “You wouldn’t like to show me, would you? It’s a long time since I’ve seen one so young and virile. You never know, it might bring back some old memories. Would you show me?” She looked back at me.
I nodded, my mouth suddenly dry. “Go ahead,” I invited. “All yours.”
There wasn’t a single word that I could utter as I watched Lisa competently reach down and undo my belt with a firm pull and a quick un-clipping of the buckle. She pulled away the ends of the belt, undid the metal button on the waistband and found the tab for my zipper. She pulled the zipper down with a deliciously slow movement, leaning over a little as she reached down to get it fully undone. When she completed the move Lisa pulled away the sides of my jeans, giving her the widest possible view of my briefs and the bulge they were barely containing.
“It’s always so exciting, seeing a new one.” Lisa looked back to my face, smiling, while she extended a finger and let it gloriously trace my length through the taught material of my briefs. “It’s been a while since I saw a new one though, so this is doubly exciting.”
She looked back and watched her own finger moving up and down the silhouette of my excitement. “Do you like that?”
I swallowed back my first attempt at speaking and managed to say, “Yes. It feels good.” My overpowering desire was that she took me tightly in her hand, but I think she knew that and was enjoying the moment in a more mature way.
“So, let’s just lose these, shall we?” Lisa pulled on the sides of my jeans, motioning that I should ease my body up so she could remove them down my legs. I pushed my hips up and then, when she had my jeans at my knees, lifted my feet so she could pull them away. Now I was sitting back again, my pants still on and Lisa’s hand back rubbing slightly on me. I just watched, mesmerized by the sight of the wrinkled skin on the back of her hand moving and feeling an incredible excitement continue to build.
“Let’s see then.” Lisa repeated her movements, pulling at the sides of my briefs, and encouraging me to help her remove them. She had to move a hand to pull the elastic waistband over the tip of my cock, but then pulling my briefs away was an expert move that I completed by shuffle them off the ends of my feet. Again, I settled back, this time knowing Lisa was taking in every detail of my exposed cock.
It was a few seconds before she spoke, or touched me. It felt like she was just looking and enjoying the moment, while all I wanted was for her to pick me up and relieve some of the tension she’d helped build up. I looked down and saw my foreskin not quite covering the head of my cock. I twitched a couple of times under heat of the dual scrutiny.
“I love an uncircumcised penis.” Lisa’s use of words jolted me a bit, I was more used to the slang “dick” or “cock”, but any thoughts of that being unusual disappeared when she reached down and wrapped her fingers around me.
I watched as she slowly lifted me up to be almost vertical. My foreskin retracted a bit further, exposing more of the head, and then she pulled down and exposed all of the head. “There. I’ll bet that feels better.”
“A bit.” I gave a nervous laugh. “It feels good.”
“Do you want me to stop touching you?”
I gave a slight shake of my head and Lisa smiled. I felt her hand stroke me once before she turned back to watch my cock in her hand.
“It does look like you’re quite excited. Do you want me to relieve you?”
“Oh God.” I groaned, feeling her hand stroke me while the other reached over and dug down in my crotch to release my balls to her touch.
Lisa gave a small, sympathetic laugh, “I’ll take that as a yes.”
There was no way I was going to last long. Lisa’s assured and sexy moves had me close to cumming already and now knowing for sure that she intended following through on her suggestive movements was another boost to my building excitement.
“Relax.” I heard her instruct me and chuckle. “I think I remember how to do this.”
I wasn’t going to disagree with that. Her strokes on my cock were long and slow as her other hand squeezed and released my balls in time with her strokes. Lisa held my cock vertically, pushing away from my belly and heightening the pleasure of every stroke she made.
As I tried to concentrate on watching the movements of Lisa’s hands on me, I felt the first stirrings of orgasm start to creep along my thighs. I groaned and closed my eyes as the feeling built, rushing along my nerves and flushing that familiar white hot pleasure through my veins. There was nothing familiar about the intensity of this one though.
The climax felt like a nuclear test in my balls. Big, rolling waves of heat and pleasure washed through my muscles and nerves as Lisa continued with her slow strokes and looked back to see my face as I came. After the orgasm had been in full flight for several seconds the first spurt of cum jumped a couple of inches out of the tip of my cock, followed by several much stronger streams that jetted out while Lisa milked me. After the final spurt she squeezed me tight and pulled up so the last of my white cum seeped out.
There was cum all over my thighs, my cock, her hand and the sofa but Lisa made no motion to clear anything up, she simply held my cock tight and smiled at me. “That’s better?”
I nodded, still feeling the last shivers of orgasm in my thighs. There was no doubt that for whatever reason, my inexperience, inexperienced partners, that had been the biggest climax of my life so far. I was pretty stunned by the intensity and length, mesmerized by Lisa’s hand on my cock and numb at the event as a whole. There are moments in your life when you just want to lie there and soak it all in – this was one of those.
“I think I made a mess here though.” Lisa looked around at the white splashes of cum everywhere. “You certainly had a bit stored up there young man.” She laughed. “Let me get a towel.”
Lisa quickly got a hand towel from the kitchen and wiped her hand before wiping down my thighs and cock. She felt like a nurse, tending to me in the aftermath of a trauma. While I didn’t feel exactly traumatized, I did know I was in the aftermath of something.
“I’m sorry about the mess.” Was my weak offering as my voice returned.
“Oh, don’t worry about that. I’m just glad you enjoyed. It certainly looked like you needed that.”
My cock was softening, but not truly soft yet and I still felt a strong excitement in the situation. I wanted to prolong the situation with Lisa but really wasn’t sure in any way how to ask her what she wanted, or needed, even though I was pretty sure by now that whatever she wanted would be in my best interest.
I needn’t have worried. When she was finished mopping up my cum, Lisa lifted my cock again, almost like she was feeling its weight. “Almost feels like you’re getting hard again.” She looked back at me and smirked. “Wasn’t that enough for you?” She held my cock vertical again. It bent over a little, but twitched. “You young boys. You’re just insatiable. What can we do with you now?”
Lisa looked at me, meeting my eyes, smiling, suggesting. All I had to do was say. It was so different from the persuading and pleading I’d been used to with girlfriends. “Do you…” Even knowing I was on solid ground, I was reluctant to say. “Do you want to feel it inside?”
The smile on Lisa’s face widened. “I thought you’d never ask.” She bent over and kissed me lightly on the lips. “Come with me.”
She took my hand and led me up from the sofa and through to her bedroom. With her free hand she pulled a comforter from an open box and threw it on the mattress. While she spread it out and smoothed it down, she motioned to me to get a couple of pillows from a pile on the corner of the room. When we were done preparing the bed she instructed, “Take your shirt off, lie down. I’ll be right back.”
Lisa went into the bathroom and I heard running water, some undressing noises and the clink of what I later learned was mouthwash. She came back into the room naked.
“I hope my body isn’t a turn off for you.” She looked a little unsure of herself for the first time. “I’m no spring chicken, but I don’t think I’m terrible.”
There was a little extra weight around Lisa’s hips and her breasts sagged just a bit, but there was no doubt in my mind that she was in great shape for her age. I looked between her legs and saw a bush of pubic hair. “You look great,” I said, meaning it.
Lisa climbed onto the bed, one leg at a time, allowing me to see better between her legs and catch sight of her large pussy lips for the first time. “I’m glad. I’m sure you’ll enjoy. I can’t wait to feel you inside me.”
I took that as a cue and started to get up from my prone position on the bed but Lisa pushed me back down. “No, no rush. Just lie a moment.”
She kneeled facing me and took my cock in her hand, gently stroking it in a comfortable, now familiar motion. She watched her own movements intently as she slowly explored every inch of me, stroking the skin, running her fingertips along me and squeezing around the rim. At the base of my shaft she massaged a little more deeply, sending wonderful sensations down into my balls and all around them. I saw a smile cross her face as she noticed the bead of pre-cum that had appeared at the end of my cock. “We have plenty of time. I want to feel you inside, but I want to taste you first.” Lisa brought her head down to my cock, gave it a small kiss on the tip and then slipped her mouth over me.
Her lips closed tightly over my shaft but the inside of her warm mouth was wet and her wandering tongue made some delicious, slow, movements that massaged my shaft as she moved up and down on me. I felt the warmth of her mouth spread all over me as she sucked and licked at me lovingly.
When she popped me out of her mouth I looked down to see the glistening head still firmly in her hand. Lisa’s eyes didn’t leave my cock as she lifted it, stroked it and caressed it. She pulled my cock upright so it was almost vertical from my prone position and licked me up and down again while she let her hand press firmly into my belly and wander around my thighs.
As I watched her movements on me my excitement continued to build and I realized that I was on the brink again. “I’m going to…”
Before I’d spoken Lisa had taken a firm hold of my cock and pinched hard around the rim. “No you’re not. I have you.” It was like she was a step ahead of me, in full control.
The imminent feeling of climax waned slightly and I sighed in relief. Lisa let go of her hold on my cock when she knew I wasn’t going to cum, and then she shuffled back on the bed and invited, “Why don’t you come over here and touch me a little.”
It wasn’t an invitation I was going to turn down and I eagerly sat up and turned to face Lisa who was now arranging a pillow for her head. My first movements on her skin felt clumsy, but her smile calmed me down and I moved up to touch her breasts with more confidence.
They were the biggest breasts I’d fondled to that point, softer and warmer than any other girls I’d had access to. When I pulled the nipple between my fingertips Lisa gave a small gasp and closed her eyes. Her nipples were bigger than a quarter and pretty flat, but as soon as I tweaked her it came to life and stood out. I let my other hand duplicate my movements on her other breasts and Lisa opened her eyes and as, “Suck me baby. Suck them a little.”
I eased my head down and looked at her breasts momentarily before taking one of her nipples in my mouth. I let my tongue run around her excited bud and sucked hungrily on her, feeling the nipple swell a little more under the influence of my movements. I moved over to the other nipple, leaving my fingers on place to continue to work the first one. Again I marveled at her stiffening on my mouth and smelled Lisa’s fresh skin for the first time. It was a simple, soap smell, but it was a smell I would remember for the rest of my life.
“God, that feels good.” Lisa’s voice had suddenly become breathy now. “Here.” She took hold of my hand and led it down her body, “Touch me, feel what you’ve done to me.”
She was soaking. I had never felt a pussy that was so wet. As I tried to run my fingers along the opening between her pussy lips my fingers slipped easily inside her and as I pushed two fingers deeper into her Lisa gave a long, low moan of pleasure.
As easy it was to slip into her wet hole, I noticed that Lisa’s pussy was tight enough to squeeze my fingers once inside her. I made a few in and out motions, then pushed up hard towards her tummy while I sucked hard on her nipple. Lisa’s hand came up to my cheek and caressed it lightly while she whispered, “That’s so good baby. You do that so good.”
I wanted to continue with my fingering her and had just found her clit when she decided the time had arrived for more. “Inside. I need you inside me. Fuck me baby, do me hard and good.”
Lisa opened her legs wide as I shuffled between then and leaned over so my cock was positioned towards her pussy. She reached down and took a firm hold of my shaft and pulled firmly towards our goal. Her other hand joined the first, one on either side of me as the head of my cock arrived between her swollen pussy lips. She paused there, seemed to rub the head of my cock in her juices and then pulled her hands away, leaving me to push into her.
It was easy and oh so incredible to sink into Lisa’s body. I pushed in as far as I could and as I reached the deepest fractions of her she pushed up to meet me, making sure I got as deep as possible. “You feel so hard.” She breathed in my ear. I can’t believe how hard you are.”
The whole world seemed to be our bodies as I started to move in and out of her. At first I pulled out as far as I could, almost slipping out of her a few times, but as I built up a rhythm my stroke was less, but firm. I felt Lisa squirm under me, always making sure she got the best position to feel the way she wanted.
I first knew she was close to cumming when she reached around and used her hands to pull me hard into her body. With every stroke she held me close into her, pushing her bodies tight together and encouraging me to thrust deeper and harder against her pubic area. I heard her groan and noticed a slight let up in the pressure she encourage me to make on her and I knew that she was on the brink, now only needing a small push to go over the ledge to her climax.
I didn’t slack off thrusting into her as she came, Lisa just breathed harder and harder under me until the moment burst and every muscle in her froze. Lisa’s eyes opened wide in sheer pleasure as the waves of her orgasm pounded through her body. I kept thrusting, watching as she shook and feeling the spasms of her pussy around me. Her pussy contractions seemed to go on and on and I only knew that her climax was finished when her eyes softened and she smiled up at me.
“Oh my. That did feel good.” She pulled my face to hers and forced me to pause thrusting while she kissed me on the lips. “You dear boy. That was just what I needed.”
I made a move to roll off and stop thrusting but Lisa caught me immediately. “No, no. Keep on. I want you to cum again. I want to feel you cum inside me.”
I paused a moment, wondering if I should ask a question about birth control or something but she’d read my mind again. “It’s okay, go ahead. Cum for me.”
If there was any pressure in her instruction, I didn’t feel it. I did feel her hands as she wrapped them around my back and started to move over my skin. With each thrust she moved down to my buttocks and up to my sides, tracing her fingers over tender parts of my skin and quickly raising my excitement back to crucial levels.
Lisa was verbally encouraging me as I pushed in and out of her but by now I wasn’t hearing a thing, I was simply following my body’s desire, fucking her.
With all of the excitement of the last hour, it wasn’t long before I felt myself cumming again. Our movements had brought me to the brink and another huge climax was building in my balls. As the pressure built quickly I knew it was only a matter of seconds before I came, and the, with one final thrust into Lisa, the dam burst.
My head exploded before my balls did; an intense, light-headed, fog surrounded me for a few seconds as all other feeling gave way and only the burning pulse of orgasm, rushing through my every vein was left. I felt my cock start to twitch as my thighs spasmed with the climax. Moments later I started to shoot a fresh load of white hot cum into Lisa, unloading with an unexpectedly powerful release. I had no idea it was possible to orgasm so intensely so soon after the first one.
I slumped back on the bed and we both started up to the ceiling, catching our breath and letting the reality of the moment sin in. Lisa was reading my mind. “Don’t you dare,” she admonished, “ask me not to tell your mother.” She laughed at the thought. “I’m not that stupid.”
“Good.” I panted. “I won’t tell either.”
She leaned over and kissed my cheek. “I’m sure this wasn’t what either of us expected today, but it sure was a nice thing to happen.”
I looked into her eyes and held them for a few moments. “It was wonderful.”
My mother picked me up early that evening. Lisa had showered and I had redressed and pulled myself together after the exertions and pleasures of the afternoon.
As I was leaving the apartment Lisa called out softly, “Thank you so much for all your help today. It was nice to see you. Come around any time you like. I always have soda in the fridge.” She made it sound like the invitation she might give out to any acquaintance, but I caught a glint in her eye that I’m sure was only there for me.
My mother had no clue.