Samantha From My Past: The Nightcap

This story is a fantasy featuring mostly heterosexual female on male sexual encounters, mostly older participants. Any similarities to real persons is unintentional. All characters are of age and consenting. This is a long read, not a quickie. Slow build to, hopefully, a good payoff. Reflects the author's preferences and proclivities. Not for everyone. Enjoy. If not, thanks for giving me a try; there are many other great stories and authors to enjoy here.

Might be good to read the previous stories for context: Samantha from my past -- the bike, the boat, the bar, the run, and the bed.

After our sex session, subsequent showers (separately, I might add), and after our dinner, the three of us had a quiet evening sitting on the front deck looking at the lake and the glow of the sunset on the hills across the lake. By the time it was truly dark outside, and the mosquitos were making themselves known, we had managed to polish off two bottles of wine and a late-night espresso martini, which had seemed like a good idea at the time.

There had been hardly any touching leading up to bedtime that evening, other than brushing past each other in the kitchen as we had prepared dinner. No kissing, not even hugs. Just warm and comfortable company. Almost like we'd expended all of our intimacy in thirty minutes of raw sexual energy. There were some comfortable silences together, in between conversations.

I for one was reeling internally. But the two of them seemed normal, comfortable, conversational, funny and lighthearted. Like nothing had happened, and like we'd known each other for years. I think we were all relaxed, tired, worn out from the sun, the pool and the intense sexual experience we'd shared.

My mind was a jumble of images and emotions.

The previous four or five days had been incredibly intense. Adding Anne into my brand-new sexual relationship with Sam had been surprising and delightful. I'd gone from years without any sex, to sex almost every day for five straight days. Peaking with a threesome that introduced me to many new experiences. I'd held my own, but I was mentally and physically exhausted. That was my first time being with more than one woman, and the first time I'd ever watched two women pleasure each other. I hadn't cum this much in years. I was craving electrolytes, and had been drinking water like crazy since we'd finished our heady session in the guest room.

It was complicated. Sam was cheating on her boyfriend with me -- and with Anne for that matter - and was clearly conflicted about her relationship with him. She'd indicated many times to me that she was frustrated, and she felt that their relationship was "over". But in my experience, those statements sometimes proved to be hollow after time passed. I couldn't say one way or the other if she would break things off with Jeff. I also didn't know where I stood with her from a long-term perspective.

All I knew was that I'd had a summer fling with a gorgeous woman. We enjoyed each other's company -- with what little time we'd had together.

Given that we'd had several previous social interactions in the years before she left her husband (or he left her) and before my wife passed away, it felt like we'd known each other a long time. But we still didn't know much about each other. Other than intimate knowledge of each other's bodies.

Sam and I had sucked and licked each other's bodies, drank each other's fluids, fucked, and even shared our passion with a third person: Anne. We'd been together clothed in cycling spandex, tight swimsuits, summer attire and buck naked. We'd orgasmed multiple times from each other's touch. I'd bathed her in my prodigious seminal fluids. I'd buried my face in her hot snatch and she'd bathed me with her delicious cunt juice. She'd worn a pair of thong panties that I'd drenched with my jism. She'd washed my cum off the chest of her sexy green bathing suit. I'd washed our fluids off the floor of my kitchen, and laundered a duvet and pillow case that had been soaked in my cum, her pussy juice and that of her friend Anne. Anne was a gusher, and I had some carpet cleaning to do in the spare room once they left.

And yet before bed we had spent the evening talking and laughing together like three old friends. Neither Anne nor Sam shared too much about their personal lives, mainly talking about world events, travel, future plans, business and even some politics. Anne didn't wear a ring, but I didn't know if she had a partner -- of any gender. We just were comfortable with each other. In a way I was unfamiliar with. They were very at home with each other's company, and became more comfortable with me over the evening. I tend to be a shy and retiring person in groups of people, but I felt very friendly with them, and tried to be as outgoing as I could. It was the most conversation I'd had with Sam this whole weekend. We'd spent more time cumming on each other than we had actually spent talking with each other.

After we had bid each other good night, and gotten ourselves much-needed glasses of water, we each headed to our rooms. I had shut off all the lights in the house and checked all the doors before heading to get ready for bed. The girls were apparently sleeping in separate rooms.

I had changed out of my clothes, had my second shower of the evening -- a short one to get the smell of the grill off me, and had dried off. I was in my comfortable loose boxer shorts, standing at my sink finishing brushing my teeth when there was a quiet tap on the half open door of my ensuite bathroom. I turned and Sam was standing in the partially open doorway, smiling at me. I rinsed my mouth, spat and turned off the tap, wiping my face on a towel. The light was soft. The mirror backlight the only illumination.

"Hey."

"Hey". She was in a loose red t-shirt that fell to the top of her thighs. Barefoot on the warm floor. Hair a little damp from her shower. "Thought I'd come and say a proper good night."

"Can I come in?" I nodded. She came toward me and reached up on tiptoes to give me a soft kiss on the lips. Her hands rested on my hips. I put my arms around her.

"Thanks for having us over for dinner and a sleep over".

"My pleasure." I could smell her, clean and fresh. Eyes a little misty from the booze and the later hour. She held my gaze.

She pulled me into a hug and rested her cheek on my chest. "Are you OK with today? I mean...With everything?" I understood what she meant.

"I'm definitely Ok. If you two are, of course."

"Oh yeah. We had fun." She squeezed me tight. A moment's pause. "I don't want to leave you tomorrow."

There was another short pause as we hugged and rocked a little. My cock throbbed slightly in my boxers, coming alive pressed against her stomach. She would have felt it.

"You're both welcome to stay another night. Tomorrow." I looked down at the top of her head. Her hair cool and damp against me. She squeezed me tighter.

"Thanks." Then looked up at me. "Let me see how we feel tomorrow when I'm not so full of wine and martinis." Smiled. "I also am looking for a hair-dryer."

"There's one in the bottom drawer of your bathroom vanity." I thought for a moment. "It could be buried under washcloths."

"I'll have a look, thanks."

She pulled away from me and looked down. "Someone's coming alive." Placed a hand over the thick tube in my boxers. Then: "Mmmm" as she caressed me gently through my shorts. She tugged my boxers away from my waist and put her hand down onto my fattening flesh. I looked down. She grasped the base of my penis in her small hand and swung it slowly back and forth, flapping it around softly. It moved against the material of my shorts, swaying like a hidden beast behind a curtain. The clearly-defined ridge of my glans was visible through the thin cotton. She gave me a squeeze and my cock reacted by throbbing in her hand. It was growing.

"Mmmmmm" she moaned again.

"Can't help myself." I breathed out.

She looked up at me through lowered lashes. "I think I might help myself."

Slowly, she lowered herself to her knees on the plush mat laid in front of my sink, pulling my shorts away from my organs and down to my ankles. I kicked them off. Here we go again.

She held my lengthening cock in one hand and softly stroked the back of my huge sack, gently kneading my heavy balls with a thumb.

"God this thing is so thick." Looking at my dong and then up at me. Then whispering: "I love your big cock." It looked massive in her tiny, manicured hand.

"I don't know how much more I have to give." I sighed. "I'm pretty spent."

"We'll see about that," she smiled, then leaned in slowly and pressed her lips to my testicles where they swung heavily from below the base of my cock, alternatively licking and kissing them gently, holding my penis above her face out of the way. It lurched in her hand and I steadied myself on the bathroom countertop behind her head. Her small hands made my big thing look even bigger. It stretched in her grasp as she focused on my balls. Her tongue softly tickled around the bottom of my sack as she used one hand to gently squeeze behind them, stretching the hairless skin taught as she slathered them with her saliva. Her other hand started to pump at my rod, teasing it firmly from root to tip. My heart began to thud in my chest. I grunted.

"I think you've got a nightcap in here for me." She spoke softly, seductively, alternatively looking up at me and at my large organ in front of her. She lowered my cock down slightly and ran the end of her tongue around the tip. The purple head of my penis was too big for her small mouth -- as we'd already established - so she began lovingly sucking around my piss slit. Soft gentle tickling of her lips and tongue on the sensitive underside of my cock head, and back around to the end.

We heard a slight noise at the bathroom door and both turned our heads. There was Anne, smiling. Large mouth and soft lips framing bright white teeth. Lipstick washed away in her shower. "Here you both are." Slyly. "What a surprise." Sounding not surprised at all. "Did you ask him about the hair-dryer?" She cocked an eyebrow.

She was in a t-shirt as well, too short, exposing the crotch of her red thong underwear, tiny straps around her sexy hips. The pink shirt hugged her large fake breasts, perfect in their heavy roundness. There was a picture of a toy bear stretched taught between her peaked nipples. Long cones at the very tip of her tits. She looked like a porn star. A cougar ready to pounce.

Sam said: "There's apparently one in my ensuite."

"Oh, great."

She walked towards us and came behind me, wrapping her arms around me and pressing her chest into my back. In the mirror I saw her get up on tip toe behind me. With one hand she gently walked her fingers down my naked torso and under my testicles, gently grasping them and moving Sam's fingers away. With the other hand, Anne grabbed the base of my cock and brandished it in Sam's face.

"Let me help you two with this big fuck stick." Her breath soft and sultry on the back of my shoulder, looking at me in the mirror, and then peering down at Sam in front of us.

Gently she moved her hand back and forth along my veined and bulging cock shaft while her other hand tickled gently behind my balls, alternately pressing in and up on my taint. In the mirror it looked like I was jerking my cock off with someone else's thin, tanned arms.

Precum glistened at the tip of my penis. Sam moved her own hand to the head, fingers firm behind the ridge of my glans, her lips and tongue on the tip licking at my secretions. Softly slithering around.

I was lost in the sensation of being so sexily massaged by these two minxes. Their hands moving back and forth, plenty of room for both of them along my big rod. Anne's nipples feeling firm against my back. Out of nowhere, I was brought into the heat of their sexuality. It seemed to come to them so easily. So comfortably. One minute I was brushing my teeth and the next I was hard and ready to spray my load into Sam's pretty mouth.

I breathed heavily as Anne increased the pressure behind my balls and gripped my shaft firmly like the handle of a baseball bat. Veins popped along it's ridges. In the mirror above the sink I could see her looking around my shoulder, down at Sam's face. On her knees, Sam looked dwarfed by my nine-inch rod, sticking out of her mouth. Looking bizarrely huge. Behind Sam's shoulders, I could see her taught firm ass cheeks peeking out from under her tshirt, sitting on her own feet. No underwear.

Gently, Anne removed her hand from my balls and I felt it move back between us, between my bare butt cheeks and her own soft body. She kept her other hand on the base of my cock. Gripping me firmly like a warm cock ring. I heard the quiet rustle of fabric, soft snap of elastic, and felt her wrist moving around behind me, fondling her own sex. In a moment, I could hear the quiet moist sounds of her fingers digging in her pussy. I looked down at Sam and she glanced up at me. Gave me a small smile. Then without breaking eye contact with me, I watched her slowly reach two fingers down to her own crotch. I let out a long breath of anticipation, and then could see that she too was fingering herself. Sensual. Erotic. Two hot women pleasuring themselves and me at the same time. Sam knew what I liked. Probably more than I did.

I closed my eyes, one arm propped on the counter, and the other hand resting gently on Sam's hair as her face moved back and forth on the tip of my cock. Soft sounds of pussies being stirred. The gentle smack of Sam's tongue and lips on the engorged head of my penis. Both women softly moaning as they pleasured themselves and me.

I could feel my sack rising up towards my groin, as the familiar tingle shuddered through me, my cock rock-hard in Sam and Anne's grasping fists

Anne removed her hand from her pussy and slowly brought it in front of me, and up to my lips. I opened my eyes and reached out a tongue to grasp the tip of her index and middle finger. Soft fragrance of her excitement, fresh from the shower. And then Sam's hand reaching up to me and presenting her middle finger as well. Heaven.

I opened my mouth fully and both women dipped their glistening digits into my mouth and I tasted them, my tongue slathering over their fingers. Aroused women, both musky and sexy. Their scent overpowering me again.

"Unnnngh! Oh fuck. Mmmmph," breathing through my nose as I licked and sucked their delicious fingers. I saw dots in front of my eyes and suddenly my taint pumped and I erupted.

Sam was sucking hard at the tip of me, as the first large ropes of my semen burst into her mouth. Anne's hand working its way forward and back along my shiny cock shaft. Milking me into Sam's mouth like she was desperate to fill her friend up with my cum.

Sam's cheeks hollowed, as she looked determine to drink it all. Gulping as her mouth filled with seed. My hips thrust forward involuntarily and her lips stretched to their limits, my cockhead desperate to penetrate her tiny mouth. My balls contracting with the unbelievable pleasure. Knees wobbling. Sam drank and swallowed as my body pumped buckets of cream into her. I sucked on their fingers. We both knew how much I could come, but Sam seemed prepared to get it all into her. It was so erotic. Their fingers in my mouth. Anne's body gently writhing against my back, firm breasts squished against me, her hips pressed into my naked thighs. No sounds but for my moans, and the small grunts and gulps as Sam swallowed my essence. Breathing hard through her nose, as I was through mine.

I opened my mouth finally to gasp in some air, and they removed their fingers. Anne's hands fell back behind me and she caressed my butt cheeks gently. Sam's continued to milk the final drops into her open mouth. My breathing was deep and labored as I steadied myself on the counter with one hand. The other moving softly on Sam's tousled hair. My cock softening and drooping, still thick and veiny. The sensation of her sucking mouth on my cockhead as my balls contracted had been intense beyond belief.

"Oh wow." My breathing deep. "That was ..." I was lost for words.

Sam continued to lick and suck at the tip of my cock as the last drops were milked from me with her pulling hand. Anne kneading my buttocks with soft warm hands.

One last swallow, and Sam looked up at me with a huge grin.

"How was that?" Her fingertips gently playing over the skin of my fat penis as it swayed in front of her. A stray drop of my pearly cum on her chin

"Like," I could barely speak. "Like heaven." My chest heaving. These women would be the death of me.

Anne giggled. "Let me at her." Gently pushing me aside. I leaned against the counter, naked. My cock and balls soft and pointing at the floor in front of me. A silken thread of semen stretching down from the tip of my prick. I let it drip.

Anne helped Sam to her feet, and, as though they'd planned it, Sam hopped up until she was sitting on the vanity countertop beside the sink. We were lit in the warm glow of the mirror backlight. Sam drew her ankles up to the counter as well, athletic. Her pussy suddenly wide and pinkly visible to us all. Sam beckoned me close, and I leaned in. She kissed me hard, tongue in my mouth. The taste of my cum in hers. Our kiss was long and passionate.

As we separated, eyes locked on each other: "I love drinking you. I love the taste and smell of you," she purred at me. "Your big cock is like a drug for me. I can't get enough." Briefly wrapping her fingers around my soft swaying organ and giving a gentle squeeze.

I stood back up straight. Anne moved forwards and the two women clasped each other in a warm embrace. Anne's incredible chest to Sam's small tight and muscular breasts. They kissed passionately for a few moments, Anne's tongue slathering to pick up the drops of cum off Sam's face. Their eyes closed, arms around each other. Like I wasn't there. Like Anne was congratulating Sam on an excellent performance.

Anne broke their embrace and slowly knelt in front of Sam, sitting her sexy round ass down on her own feet, thighs spread slightly, knees on the mat. Her face level with Sam's spread pussy lips. Anne moved her face into Sam's crotch and ran her tongue from bottom to top of Sam's labia. Softly moaning in the back of her throat. Sam closed her eyes and her face turned up towards the ceiling. Annes hands came up to hold the inside of Sam's thighs and her lips went straight to Sam's clitoris. Anne pursed her lips and sucked on Sam's button gently. Sam was sighing. Breathing heavily. One hand on the counter behind her, and one gently caressing her own breast and nipple. Eyes still closed. Anne reached up a hand and, underneath her own chin, inserted a long tanned middle finger into Sam's wetness. Sam was moaning, holding herself steady, and then moved both hands to Anne's hair. Perched like a pixie on my bathroom countertop. Knees spread wide above Anne's head. Pulling Anne into her pussy.

One of Anne's hands fell to her own crotch. As I watched, she inserted two fingers into her snatch and pressed her palm against her own clit. Slowly and softly gyrating her hand over her own sex.

To my surprise, I felt my cock lurch and rotate sideways to lie against my thigh, blood starting to fill it. I knew I couldn't get a full erection so soon after blowing my load. So soon after Sam gobbled down my gallons of ejaculate. I reached for my organ and idly ran my hand along the shaft, back and forth. Pretending to myself that I might get hard again. I couldn't help myself. They did it to me.

The bare sexuality of the two hot women was overwhelming me. I could still taste their delicious pussies in my mouth. Savoring their musk and scent. The end of my cock flopped, still long in my hand, not having retracted to its usual fat six-inch soft state. My brain was still firing, almost on impulse. I watched Anne press her tongue flat against Sam's clitoris, humming a little. Sam was bent in two up on the vanity, holding Anne's hair as her sex was attacked. Sam began slowly to grind against Anne's face. Moaning. Anne's finger continued to gently fuck Sam's hole. I could smell Sam's pussy, delicious and familiarly strong despite her shower.