My Long Weekend With Mom
Growing up, it had always been just Me and my Mom. She had me really young, when she was in the middle of doing school. From what I know, she was in a relationship with my father at the time, but it had always been unstable and she left him shortly after finding out she was pregnant. She has always been Superwoman in my eyes, but looking back; I don't know how she managed it all. With raising a k**, finishing her Master's degree and being a working Mom being just the biggest of her concerns; she always seemed to find a way to make things work. I can remember the handful of relationships she had. I also remember that none of them ever lasted. They were all her age, which meant that they just weren't "dad" material. She hadn't been in a relationship since I was about 10 and, other than occasionally dating, I was the only consistent male in her life.
Holly and I have always been extremely close and as I started getting older, that only intensified. Now I'm in college and living a couple hours away; but between school and life, I manage to make it home at least every couple of weeks. When I am home, I take care of Mom in all the ways a boyfriend or husband would I guess: if she had either. I don't typically think of it in those terms, simply b/c I adore my Mom and want to take every opportunity I can to give back to her. I know that she appreciates everything I do for her, and that she loves the attention. I cook for her when I am home, clean a fair amount, and I'll even give her the occasional foot massage because that's one of her favorite things in the world. We're really great friends, mostly because of there only being 19 years between us. We hang out a lot, doing normal things; and every once in a while, I'll even take her out to dinner and to go dancing or to a movie. I love seeing her happy and I really enjoy being able to take care of her. It just makes me happy to do things for her, so I'll often go an extra mile to give her a night or two to make her feel really special.
It's not that I do things like this for her out of pity either. She has an active social life and I know that she has been seeing a guy named James for a couple of weeks now. They met at work, have been on a number of dates, and don't sound very serious. I'm currently in a relationship as well; a girl from school named Melissa, whom I've been with for almost a year. I adore her too, and am much the same with her as i am with my mother. Mom and I have always talked about anything and everything. Even about her boyfriends and love life, as well as my own love life too. We just didn't have anything to keep from the other, and feel that comfortable with each other.
On this occasion, She and I were preparing to leave for our yearly vacation together. It was going to be just the two of us in a cabin near the California coast, for four days and three nights. We've made this trip every year together for as long as I can remember.
"Hey Mom!" I call out as I breeze through the front door, dropping my keys loudly onto the table in the entry way without even looking.
Her face peeks out at me from around a corner before breaking into a huge smile. "There you are!" she cries and she launches herself into my arms, smiling playfully up at me. "You took forever getting your ass here, Ben. I was starting to think I might just have to leave without you"
Chuckling, I pull her closer and kiss her forehead. "I'm sorry Mom, traffic was a nightmare."
"Well lucky for you, I think you're worth waiting for." She smiles and hugs me like it's been years rather than weeks since I've been here.
"Can I get you something to eat, sweetie?"
"Nah, thanks Mom. I'd rather finish loading the car and get the hell out of here."
"Oh, I was hoping you'd say that!"
We quickly finish packing my stuff into her already half loaded Subaru Forrester, lock up the house, and take off.
"Are you sure that Melissa is ok with you taking most of the week?" She asks, almost uncertainly, as we back out of the driveway.
"You might have to stop asking me that, Mom." I chuckle. "I think that's like the tenth time in two days."
"It's just a long time and I know you have other things to do."
"Whoa, there's NOTHING I'd rather be doing Mom, and you know that." I smile at her. "Besides, Melissa thinks it's sweet; the ways I make time for you."
"Okay then!" she says, instantly brightening up.
I know better though and I smile at her: "That was almost convincing Mom." I can't resist laughing. "I think it's sweet of you to pretend that you care about whether you're hogging me all to yourself." She smiles back and laughs with me.
We continue to chit-chat for the next couple of hours, eventually lapsing into a comfortable silence. I find myself staring at her, as I often do when I am around her. I tell her all the time how beautiful she looks; knowing that it makes her feel good to have another man tell her that, even If he is her son.
"What do you see?" her typical response when I stare.
Grinning slyly, I reply. "You know, I didn't think it was possible, but I think you actually managed to get even more Beautiful while I was gone."
She blushes and giggles; "You're sweet hon, but you're crazy." Mom never thinks that she's as good looking as I tell her; and she doesn't really think she's anything special. Something which has always really bothered me. I see the way she gets noticed by men whenever we go somewhere. Even I've always noticed Mom; aware of how very sexy she is. I couldn't help noticing sometimes. Particularly her perky 36a breasts, whom she loved to leave braless just about all the time. But especially under her skimpy, strappy tank tops and sundresses. I mostly just shrug it off though. I've never really given it much thought and just attributed it to being a "guy-thing"; noticing something like that, regardless of who the Woman it might be.
"That's ok Mom, that doesn't make me any less right about you." I pause for a moment. "Besides, you deserve to hear how good you look."
"You always know just what to say. And with lines like that, it's no wonder you landed Melissa." she turns to look at me. "You look really handsome, by the way. I like how you look when you don't shave for a few days."
At that, I just laugh and continue to watch her as she drives. I'm nothing special to look at. I'm average looking, in my own opinion. I'm 21 and six feet tall with broad shoulders. I have short brown hair and the same brown eyes as Mom. I'm in pretty good shape, being a runner myself as well. I do alright with Women, but I'm not the type who just looks to score, I'm more of a relationship guy. Probably the real reason I won Melissa over.
Holly on the other hand, has always been incredibly beautiful, as I've often used to describe her. She just turned 40, but doesn't look a day over 32. She just continues to get even more attractive as she gets older. Part of her appeal, is that experienced and sensual confidence that only comes with age in a Woman; while the other part is her bright, sparkly and outgoing personality, coupled with an energy that makes her seem only half her age. A fact that causes most people to often mistake her for my older s****r when we're together. She has a way of being subtly flirty and charming without trying, and she has these big brown eyes that just sparkle; all framed in dirty-blond hair. At 5'5, she is a solid size 10, but running 14 miles a week has given her a slimmed and toned figure with some really sensual curves......
At some point, I seamlessly transitioned from my thoughts of Mom, to drifting off. The the next thing I know, I'm being awoken by a soft hand running across my face.
"Wake up honey, we're here." she whispers
"Wha...? We are?" I groggily try to sit up. "Shit, how long was I out? I can't believe you let me sl**p Mom, I should have been keeping you company."
"Don't be ridiculous, Ben. You already drove all morning to come see me, so I thought you could use the sl**p."
"All right, thank you" I get out of the car, pecking Mom on the cheek as I exit. "How about you go get settled and I'll unpack."
"You're my hero, babe!" She grins at me for a moment, then snaps her fingers. "Make it snappy Mister! Get moving!"
I glance at my watch, seeing that it's just after 9:30pm. I hurry up an unload the car in three short trips; as we both each have a bag and a few other odds and ends that we brought with us.
As expected, I walk in the door and there's Mom, smiling up at me from her reclined pose on the couch. I lock the door behind me and drop down next to her.
"So..." I sigh. "What should we do first?"
"Hmm, you know what? I think I know just the thing." She starts to get up off the couch. "I'll be right back."
My eyes follow her as she walks around the corner and down the hall. I'm assuming she's heading to the master bedroom further back, where she always sl**ps. After a few moments, I get up to go use the bathroom, heading in the same direction. As I pass the first bedroom in the hall (mine usually), I see Mom standing there, completely naked... pulling an orange bikini out of her bag on the floor. I drink in the sigh of her perfect, sensual figure. Her perky breasts and her large, pink areolas staring back at me. Her toned tummy leading all the way down to a small, manicured triangle of soft brown hair sitting above what appears to be her shaved pussy.
I'm frozen. I've never seen her naked like that before, and my back is to her in an instant. "Shit! I'm so sorry Mom, I had no idea you had gotten up to change!"
"Fuck! Jesus you scared me Ben!" She's short of breath and from the sound of it, moving to cover up. "No, Ben, it's my fault! Jesus, I can't believe I was so careless. I... I only meant to be a second. I didn't even think to close the door."
I move back into the living room, still stunned by the sight of my naked Mother.... and excited by it too. I already feel my hard-on straining against my pants. I can't get that picture out of my head. "My god, she's even more gorgeous naked that I imagined!" I think to myself. I manage to at least divert my attention long enough to feel myself softening, just as Mom comes walking into the room dressed in a small orange bikini.
"Mom, I am so sorry, I..." but she cuts me off.
"No, it's ok Ben. I should have closed the door. I don't know what I expected to happen, I thought I would be in and out before you got up." she moves forward and wraps her arms around me. "I'm sorry you had to see me like that Hon..."
"Hey, it's ok Mom. That kind of thing just happens sometimes." I hug her back, trying not to think about her soft breasts brushing up against me. I change the subject. "So, what was your big idea Mom?"
She's blushing when I look down at her and she looks up at me uncertainly. "Are you sure you're ok Sweetie?"
"Of course I am Mom." Now I pause hesitantly. "...Are you ok?"
She smiles, seeming relieved. "Definitely. Now come on, the owners added something since the last time we were here." She takes my hand and leads me through the kitchen. Pausing only to grab a bottle of chardonnay from the fridge and two glasses. "It's out in the back. I think you'll really enjoy this." She hands me the bottle. "But first, would you open this for me please?"
Taking the bottle from her, I smile at her. "Wine? What's the occasion Mom? You seem awfully excited about this."
"Why wouldn't I be excited to be sharing the better part of a week with my Son?"
With that, she turns and exits the cabin, leading me by the hand out into the back yard.
As I follow Mom out into the yard, I see that the owners have added a hot tub. She's already at the tub, placing the glasses on the edge. I can't help but stare at her perfect ass and even between her thighs, as she raises a leg over the edge of the tub and slides in.
"Aaaahhhh....." She sighs; "God, it's the perfect temperature. Hurry up Ben."
I chuckle. "Hang on, let me go grab my suit." Setting the bottle of wine down on the deck by the tub and turning towards the house.
"Oh, just wear your boxers Babe. It's practically the same thing. Besides, you're already out here. Right?"
"Are you sure Mom? You wouldn't mind?"
"Of course not, Ben! Don't be ridiculous; just get in here!" She declares happily.
I slide off my pants and my shirt, leaving them on the ground before making my way over to the hot tub. I pause to reach down and activate the jets before climbing in.
"Oh, shiiiiit! Those feel amazing on my back." Purrs Mom, who's already sunk in up to her chin.
As soon as I settle, she moves over to curl up next to me; putting my arm around her and laying her head happily on my shoulder. "Would you pour me a glass please Ben?" offering me her empty glass. I happily fill both and return hers.
With the jets pounding on my back and Mom nestled in next to me, I'm completely comfortable. The water does feel good.
"So, tell me how you are Mom. You haven't said much about what's going on with you since I got here. You're still seeing that James guy, right?"
"Ugh, I'm ok I guess." she sighs unhappily. I can read her well and I notice that she's already nearly finished with her wine. "Oh! Well I'm convinced Mom" I tease. "Seriously though, talk to me Mom."
"Well, James is nice enough I guess... but he's rather tame. He's just so... button-down. Not my usual type at all. We're up to our seventh date, and..." She hesitates; and when I look down, I see that she's blushing again. "Oh, I can't believe I'm saying this; but he hasn't even tried to make a move yet!!" I can instantly hear that there's more in her voice than annoyance. I can hear the hurt there too.
"What? Um... Well, did you ever think that maybe he's just trying to be a... gentleman? I guess?" I offer her a refill and she accepts. I fill mine again as well.
She doesn't respond, but just leans against me in silence; drinking her wine and sulking. After another few minutes, she holds her glass up for a third refill. "She must really be upset about something." I wonder to myself as I fill both glasses for a third time.
By this time, both Mom and myself are beginning to feel the effects of the wine. I shift my weight and turn so I'm facing her. I wrap my arm around her waist and pull her to me. "Ok, you're going to have to talk to me now Mom. Something is bothering you and we both know it. Out with is s****r." I tell her softly, kissing the side of her head.
My words break her reverie and she turns to look at me. "I really can't hide anything from you can I Ben?" she sighs, "Ok. It's just that, after all this time, I would have expected SOMETHING from James. I mean even an actual kiss for Christlike! More than just a kiss on the cheek goodnight. I... I guess that I'm just worried that... that I'm losing my touch." She blurts out; and at this, I hear her voice break.
"Sshhh.... That's not true Mom. You are absolutely gorgeous. In fact, I think you are even prettier and..." I hesitate before taking a deep breath. "...and more sexy now. Even more so as you get older."
She looks up at me quickly and I can't read the look in her eyes.
"I'm sorry Mom... I... I hope that doesn't sound weird to say to you. I... Shit, I'm sorry Mom." I turn away from her.
"No, don't be.... Look at me Hon." Mom says quietly, turning my face back to her. "I think that's unbelievably sweet of you. It means a lot to hear you comfort me like that. You know, you're really the only man who I hear things like that from... I mean, James says nice things occasionally, but he doesn't have your way with words. The way you always make me feel so special Sweetie." She gives me a long kiss on my cheek.
Taking a deep breath, she continues: "I... I just feel so lonely sometimes. I've been on several other dates with men other than James, but I just feel like I keep striking out." She's a little pouty at this point, as she scoots back from me to fill both of our wine glasses again. Returning to her spot, she breathes. "I just need someone to touch me again! You know... intimately. I'm sorry sweetie, I know how it must sound to hear your Mother talk like this but..."
She pauses again to take another long drink from her glass; actually draining half of it at once. I am already feeling a strong buzz, so I know that she certainly is too.
Setting her glass down, Mom does something that I never saw coming. She takes my face in her hands and kisses me. Not just a peck on the lips, but a long, passionate kiss. Her tongue eagerly exploring my mouth and meeting my own tongue. All 7-inches of me is instantly rock hard; straining to free itself from it's cotton prison. All too soon, she pulls away.
Mom looks in my eyes; nervous and uncertain, she whispers so only I can hear. "Ben... I... Did you like what you saw earlier? You know... When you walked in on me?" She won't look at my eyes now, afraid of the answer.
I know I should hesitate here... She's my Mom for fuck's sake! "God, yes Mom! I know how that must sound, but... I haven't been able to stop thinking about it." I blurt out. She looks up at me now, but her eyes are different. There's a subtle, smoldering fire in there. I't a look I've never seen in her before.
"...Do you want me Ben?" She asks in a tone that manages to sound both seductive and uncertain at the same time. I feel shivers run down my spine, listening to her.
"I... I... Oh god, I do Mom! I want you. I want to be the one to take care of you." I finally manage to stutter, my thoughts a blur.
"I want you to call me Holly, ok baby?" She breathes into my ear; and with that, I'm kissing her. Our tongues once again dancing together, frantically exploring the other's mouth. With my left hand, I begin to slide it slowly up her tummy, finally caressing lightly over her breast. My hand lingers there, gently squeezing and massaging it before moving on to her neck; eventually resuming it's course around her body once more.
Holly is moaning quietly in her throat now as I continue to kiss her. I eagerly explore the rest of her incredible body, never breaking that connection. My cock is so fucking hard.... I can't take it. I finally pull back from her, breathing like I just ran a marathon. She's flushed and breathing equally hard. I shift my weight and slide my boxers off, tossing them I don't know where.
Holly gasps a little when she sees my towering erection. "Oh my god Ben, you're so big! I don't think I've ever had one like that." My Mom can't take her eyes off of me now.
As I move closer, I whisper in her ear. "You know I love you, Holly?" I feel her shiver all over as I run my fingertips up her back and untie her top; then moving to the neck and pulling on that too. It falls away and I immediately drop my face to her breasts, gently sucking her now firm nipples, alternating and lightly pinching them.
Holly is moaning louder now, more continuously. She's so turned on right now. "God, Ben. Jesus! Don't fucking stop Baby. Oohhh...." Her body shudders again as she digs her nails into the back of my neck.
My hand now roams lower and lower. I feel her waistband and my fingers slip inside; where I'm welcomed by the patch of hair. I run my fingers gently over her smooth pussy, which rewards me a sharp gasp and another huge shudder from Holly. Even in the water I can tell that she's wet. I continue to tease her dripping pussy, running my fingers up and down her slit and gently rubbing her clit. I pull my hand back out, dragging the tips of my nails lightly down and around her inner thighs.
Suddenly, Holly puts her hands on my shoulders and pushes me back against the side of the tub. She immediately flips over to straddle me. My still rock hard cock begging for attention. All I can do is stare up at her magnificent body into her eyes. I've never seen this woman before, so completely consumed by her carnal needs. There are no words, only urgency and lust. I want her so fucking bad right now! Holly pulls the side ties of her bottoms and they drift away on the current of the jets. She's breathing hard as she takes my massive hard-on in a small trembling hand, lining up my head with her dripping pussy.
I put my hands on her hips and as I look into her fiery eyes, I pull her down swiftly; driving my thick cock deep inside her in one stroke. She's so wet it happens easily, but Holly gives a small grunt of pain from the sudden intrusion. I have never been in a pussy this fucking tight and it's the most amazing sensation I've felt. I watch as Holly begins pumping herself up and down in full strokes, impaling herself on my full length each time as I try to match her with my own upward strokes.
"Uhhn! Uhhn! Uhhn! Yeah Baby, just like that! Fuck me Ben!" Holly's groaning at me. Her head is thrown backwards, writhing around in pleasure. I grunt and thrust deep, before I flip her around so that I'm behind her.
"OH GOD! YESSS!" She cries loudly. She gasps again as I pull back to the head and drive my throbbing cock deep inside her again. I'm grunting loudly now as I fuck Holly from behind. I realize I can tell she's getting close, which comes as a relief, as I'm rapidly approaching too.
"Fuck me harder, Baby! I'm almost there! Don't fucking stop!" She's continually shouting as my thrusts become shorter and faster. "AAHHH!" She cries out as the waves of her first orgasm hit her. Her body shakes and she tightens her grip on my cock, which almost sends me over the edge. I manage to hold off as her orgasm passes. After a moment's pause, I continue my thrusts as I feel the end approach. She's still breathing harder.... grunting and bucking her hips.
"Oh, SHIT. I'm gonna cum baby, I can't hold it off!!" I yell out.
She turns to look back at me, still frantically grinding against me. "Do it Baby, fucking cum in my Pussy. Fill me up!!"
"AH, AH, AH.... SHIT!" I'm screaming as I give one final thrust into her and begin pumping her full of my hot cum. FUCK! I've never come this much in my life! As I'm filling my Mom up; I feel her again tighten around me, only much harder this time.
Suddenly Holly is yelling too. "Oh, Jesus! I'm cumming again!!!" As she keeps on grinding her pussy against my spent cock until finally.... it passes.
She collapses against the side of the tub and I on top of her. Neither one of us can catch our breath. Panting and dripping with sweat, I lean down and kiss the back of her neck gently; feeling her shiver slightly at my touch.
"You... That... WOW..." Is all I can manage between breaths, still collapsed against her back.
"I... know..." She replies and turns to smile up at me.
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I pull out of her and immediately, all of my cum begins pouring out of her and spilling into the water. I turn Holly around and pull her close; kissing her passionately. I then start to clean her up there in the hot tub. As soon as I'm finished, I help her out.
I look her in the eyes. "I love you Mom" I whisper to her. I pick her up and carry her back into the house, where we climb into bed together and are immediately asl**p.
I open my eyes slowly. At first, I don't remember where I am. There's light pouring into the room and I'm vaguely aware that it is not my room, nor is this my bed. Still half asl**p, I roll over towards the center of the bed and find myself face to face with the naked back of a woman. In my haze, I tell myself that it must be Melissa. Groggily, I carefully move myself against her to snuggle, so as not to wake her. After doing so, I realize that it is in fact, not my girlfriend. Instantly, I'm awake and sitting up in bed.
"FUCK! I'm waking up in bed naked, next to a fucking stranger?!" I scream in my head. My heart's racing now, as i panic slightly and run my hand through my hair. Then, looking back at the Woman; last night all comes back to me....
As if on cue, she rolls over. Just waking up, she peeks up at me from under covers; trying to decide if she's ready to be awake. Seeing that I'm awake, she smiles at me and yawns. "Mmm... M-Morning love" She says, stifling another massive yawn.
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