Night of Many Firsts
- 2 years ago
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A Night Of Firsts free porn video
The date did not get off to a good start. I arrived early as always, ordered a drink and found a nice seat outside to enjoy the amazing summer sun that for once was beating down on London. As the minutes ticked by I began to think that I’d been stood up. Suddenly, fifteen minutes late, my phone buzzed with a message apologising but assuring me she was on her way.
She finally arrived thirty minutes late and I was taken aback - she had looked very cute online but her picture really didn’t do her justice at all. Despite being flustered she was stunning, about five-foot-two with shoulder-length reddish-brown hair, hazel eyes and a brilliant smile. She described herself as thin and was not lying--hers was a tight body with a wonderful pert set of boobs and a high firm butt especially for a forty-two-year-old divorced mother of two.
As the drinks flowed we naturally chatted easily as if we’d known each other for years. The occasional flick of her hair or brushing of my arm showed just how relaxed she was in my company. I was captivated by her, and hoping beyond hope that we’d share at least a kiss this evening. Her impeccably lipsticked lips looked so inviting and I couldn’t wait to experience them.
She told me how she was brought up in New York, graduated from Columbia and had become a lawyer before moving to London seven years before with her husband. Much like myself, she had divorced a year previously and was starting out in the online dating world.
On our third drink, the talk turned to dating and sex, much to my delight. “Have you been on many dates since your divorce?” Maggie asked.
“A few,” I replied, “but not many, and how about you?”.
Much to my surprise, she said, “This is my first, and I am so nervous.”
I assured her she had nothing to feel nervous about and that I was loving her company, which seemed to relax her.
She gave a smile and asked, “And how many people have you had sex with since the divorce?”
I lied and said, “Just two. You’ve been divorced a year now so how many people have you slept with since then?”
“None,” she replied. “In fact, I’ve only ever had sex with my ex-husband.”
“You’re kidding!” I blurted out, not managing to hide my shock whatsoever.
“No, I’m totally serious. I grew up in a pretty strict Jewish home and lost my virginity on my wedding night,” she stated matter-of-factly.
Now I wanted more than ever to not only kiss her plump red lips but to do a whole lot more with this incredible lady. Sadly my hopes were soon to be shattered.
“And I won’t be having sex with you either,” she added.
Somewhat shocked at her honestly and feeling a little deflated, I cheekily replied, “Tonight, or ever?”
A sly smile reignited my hopes that maybe not tonight, but soon, I might just get to see her naked.
“Would it be alright if we kissed?” she asked, “but no tongues.”
“I promise, no tongues - unless you slip me the tongue first,” I replied with a wink.
I leant forward and closed my eyes as her soft warm lips pressed against mine and lingered for a few tantalising seconds before she pulled away. I looked up to see her smiling and preparing to kiss me again, once more delighted as she pressed firmly against my lips.
“That was nice. You're only the second man I’ve ever kissed.”
I moved closer to her and felt her hand rest on my right thigh as she moved to kiss me once more. Our lips lingered longer than ever and she released a very quiet moan. Our kissing continued for at least fifteen minutes with no sign of her tongue. As we were finishing our drinks I asked if she’d like another one or would she like get dinner.
Much to my dismay, she said she should be heading home but would love to meet again soon while her kids were still away with their grandparents. At least the possibility was there for something more and very soon, I thought. She ordered an Uber and I started walking her to the meeting point, then I felt her hand reach for mine. There we were, walking hand in hand like innocent school kids.
With only minutes to go until her Uber arrived our eyes met, I brushed a lock of hair from her face and we leant in to kiss. Our lips pressed urgently together and now my hand was on the nape of her neck, then I felt it! Her tongue tentatively pressed forward. I opened my mouth and soon our tongues were gently caressing each other as I pulled her towards me. Our bodies pressed together and for the first time, I felt the firmness of her breasts against my chest. As we parted and opened our eyes I saw her smile and lick a tiny piece of saliva from her top lip.
I leaned back against the wall and pulled her towards me, urgently exploring her mouth as she put her hands around my waist tugging us closer together. Just as we were getting heavily into making out her phone rang, jerking us back into reality. Her Uber had arrived and was just across the road from us, the driver watching us making out.
As I walked her to her car, hand in hand once more, I thought I’d try pushing my luck even further.
“Perhaps I should come with you to make sure you get there safely,” I said.
Without missing a beat she replied: “Okay, but you’re not coming inside - I told you we’re not having sex.”
“Of course not, I just want to make sure you get home safely,” I replied, secretly hoping that I might still get invited in.
The whole journey we were making out with her becoming more and more passionate, running her fingers through my hair, caressing my arms, neck and back and moaning more and more. As we arrived at her house, an immaculate London townhouse, I made sure that we both exited the Uber as I walked her to the door.
Reaching the top of the steps she turned and said, “I’ve had a wonderful evening, thank you. I’d forgotten how much fun I can have.”
Desperately yearning to feel her body once again I leaned forward, placed my arm around her and drew her in for a kiss. Our bodies pressed tightly together as our tongues danced together one final time. I’m sure she must have felt my raging hard-on against her hip. Our kiss seemed to go on forever before she withdrew and reached into her bag searching for her keys. She opened the door and turned to face me. Expecting her to wish me a good night, I was elated when she instead reached for my hand and led me indoors. This was now beyond my wildest dreams and I knew if I played it right I might just become the second person she had ever fucked.
Inside she led me to the living room and asked if I wanted a drink, which of course I accepted. She grabbed a crystal decanter and poured two fairly large glasses of whiskey and came to sit right next to me. She seemed nervous, so I put my arm around her and pulled her tight as we kissed once more. I felt her hand on my thigh, inching higher and higher - ever closer to my rock-hard cock, but never quite touching it.
I could tell she wanted more but didn’t know how to move things forward or was simply too nervous to try. Downing my drink, I stood up and said, “You have an amazing home, why don’t you show me around?”
I feigned interest as she showed me her home, hoping she’d take the hint and lead me to her bedroom. Eventually, she did, turning to say, “Other than my husband, you’re the only man ever to be in here,” smiling nervously.
“I’m honoured,” I said as I brushed her hair from her face once more and searched for her plump lips. As our tongues teased and caressed each other I tugged her hard against me, making sure to press my throbbing dick against her hip. She pulled me in, and I could feel her hands rubbing my back and reaching down to my butt but still not daring to touch it. Instead, I grabbed her ass and squeezed it firmly, enticing a deep moan from Maggie, and finally her hands clutched my cheeks. Now I knew that she wanted more, much, much more.
Mid-kiss I reached up and found the zipper on her dress and began to slowly unzip her, giving her plenty of time to object. With no objections coming, I reached up and pressed my hand into the small of her now-exposed lower back and felt her warm smooth skin against my hand. Slowly our lips parted and I took a step back, freeing her shoulders from her dress while staring deep into her eyes. She didn’t resist at all as her dress fell to the ground.
My eyes clearly gave away my delight at what I saw as Maggie smiled and tilted her head coyly at my reaction. Wow, she was even more stunning than I had thought. There she stood in an incredible set of lingerie (which I would later find out was La Perla). A black lacy push-up bra made her 36-inch chest rise ever so temptingly, more like the breasts of a twenty-year-old than a forty-two-year-old. Slowly my gaze followed down her slim figure to a matching black suspender belt holding up sheer black stockings. Her outfit was completed with, of course, a matching lace low-rise thong leaving her smooth, flat stomach exposed.
“It looks like you were expecting someone to see this sexy little outfit,” I said cheekily. “Were you hoping to get me here tonight?”.
“No, I honestly wasn’t. I wore this to make me feel sexy. I wasn’t even expecting to kiss you tonight.”
With that I pulled her close, caressing her back as I kissed her passionately. After a few moments, she pushed me back and began undoing my shirt, rushing the buttons, keen to get me undressed. Her hands explored my stomach and chest, rubbing her palms all over as she smiled knowingly at me. My shirt dropped to the floor as we pressed against each other once more, our kissing becoming ever more passionate as I began lightly kissing and licking her neck. Slowly, tentatively I felt her hands begin moving down from my chest onto my stomach again and reaching for my belt.
She quickly had my belt undone but was struggling to undo my jeans, so I lent her a hand undoing the button and pushing them to the ground - ensuring I pushed my socks off as I did so. Now she could clearly see not just the bulge in my boxers but the ever-growing damp patch she was causing. I took her by the hand and led her towards her bed. Before allowing her to sit down I reached around and unclasped her bra. For a moment she pinned her arms against her sides holding her bra in place, as if unsure. Then she moved them and let her magnificent breasts burst free. Even without the push-up bra her tits were firm and seemed to defy gravity, with firm nipples standing proudly erect.
Without missing a beat I took first one nipple and then the other in my mouth, rolling it around, teasing that bullet with both my tongue and teeth. My hands grabbed a firm handful and squeezed each boob firmly. As I stood up I pressed my body against hers and felt her now-wet tits sliding against my body. Moments later I felt her tracing a line with her tongue from my neck to my chest, licking eagerly at my tiny but now very firm nipple, sending ripples of pleasure through my entire body.
Soon I realised that she was heading further down as she took to her knees facing the throbbing cock in my shorts. She nervously took hold of the waistband, sliding my boxers off, letting my dick spring free.
“Fuck me!” she said. “It’s huge!”
Now I’ve never had any complaints about my size but never considered myself “huge”. My cock is a little over seven inches and pretty thick; combined with trimmed pubes and shaved balls, it has never disappointed - but I was delighted at her response.
I simply smiled and guided it towards her mouth, pushing it gently to her lips. Her warm and powerful tongue licked the tip, circling the entire thing as she reached up to stroke my balls. I pulled my cock up, exposing my shaved ball sac to her and felt the warm wetness of her tongue exploring my tight balls that were bursting to unload. I let my dick rest on her cheek as she finished on my sac and licked the shaft, taking it in her hand and slowly rubbing it backward and forward.
“Holy shit, you’ve got a foreskin!” she suddenly shouted. I’d totally forgotten the only man she had been with was her Jewish husband, so she had never experienced a foreskin before. I watched as she slowly pulled it to and fro, exposing and then hiding the purple head. I could see the genuine look of amazement and discovery on her face as she tugged on my dick.
“Now you’ve played with it, suck it,” I urged her.
I watched as she pulled back my foreskin letting the head free, licked it to get it wet once more and then tried to stick it in her mouth. The tip made it in, but before much else, I could feel I was filling her mouth. To give her credit, she did the best she could creating a beautiful warmth and wetness as she tried to squeeze more of my cock into her mouth. Soon she was picking the pace up, bobbing back and forth on my tip while using one hand to slide down my shaft in perfect rhythm and the other hand tugging on my balls. The sight of her beautiful face sucking me as hard as she could whilst playing with my balls was almost more than I could take and I could feel my orgasm building.
“I’m going to cum any minute if you keep doing that,” I moaned. Her pace quickened and my cock started twitching - meaning I was seconds from cumming. “I’m going to cum in your mouth, is that okay?” I begged but she just kept going. Then my balls contracted and I exploded in her mouth: first one, then another and another and one final spurt of hot cum shot into her mouth. With the tip of my cock already in there, it was more than she could take and she started to cough as cum leaked from the corners of her mouth and onto the floor. I pulled out of her mouth and she licked the cum from her lips as she recovered and began to stand.
We embraced and I kissed her deeply and passionately, tasting the last bits of cum that she hadn’t swallowed. “That was the best blowjob of my life,” I told her totally honestly after we separated.
“And that’s the first time I’ve let anyone cum in my mouth,” she replied.
I pushed her onto the bed and we fell together, our hands exploring each other’s body, squeezing, searching and probing as we rolled together. I slid my thigh between her legs and wasn’t surprised to feel how wet her panties were as she began to rub against me. I pressed her onto her back and began kissing my way down her body. I reached her luscious tits and buried my face between them, kneading the flesh of each and rolling each nipple between my fingers. Continuing on, I took one nipple in my mouth again, sucking and lightly biting it as Maggie moaned softly.
I continued south, tracing a line from her tits to her belly button with my tongue, lightly brushing my hand against her skin as I went. Past her garter belt and her stomach I reached her lace thong and tugged it down, spotting a telltale small C-section scar. She arched her back to lift her ass off the bed and free her of her underwear. Now naked except for her stockings and garter belt, I took in the spectacular view of those incredible tits, her smooth stomach, and now visible for the first time the beautifully trimmed pussy. Given her lack of sexual experience, I was surprised to see her pussy waxed smooth except for a small v-shape of pubes a couple of inches above her slit.
Tenderly I pushed her legs apart and continued kissing my way down, down to the small mound of hair, stroking her thighs, tugging lightly on her pubes.
“What are you doing?” she asked.
“Returning the favour you just gave me,” I smiled back, “I want you to cum in my mouth.”
“My husband would never do that, he always said it was disgusting. Are you sure?”
“Disgusting! It’s delicious and amazing, just relax, enjoy yourself and feel free to tell me what you like as I’m doing it,” I replied.
Moving down, I stopped right in front of her wet pussy, breathing in the amazing aroma, a mix of sweat, desire and her wetness. I blew ever so lightly, watching her pubes waft in the warm breeze as I kissed down one thigh, then back up, brushing my nose teasingly against her lips before moving on to the other thigh without touching her pussy. I could hear her anticipation each time I got close, but continued teasing, licking the areas free of pubes, taking the hairs in my mouth and pulling softly
After what I’m sure what seemed like an eternity I finally let her have what she wanted. I pushed her legs farther apart and kissed her tenderly on the lips, working my way from the top of her slit to the bottom. Once there I slid my tongue inside, relishing the moans and wriggles this elicited, and ever so slowly dragged my tongue along her entire length. For the first time, I tasted the tangy sweetness of her pussy and savoured its deliciousness. I felt her hips shift as she relaxed into it, and carefully parted her lips, exposing the hood of her clit.
Focusing my attention on her clit I leisurely began circling it and watched as the hood retreated as I progressed. Once free, I blew lightly onto her clit, then took it in my mouth as I slid a single finger into her soaking pussy.
“Yes, yes, oh fuck yes,” Maggie moaned, bucking her hips, pushing my finger deeper into her tight cunt.
I kept licking, sucking and stroking her pussy as her moans increased in both frequency and volume. She was so tight that I struggled to get a second finger inside her, but once I did she went wild, rocking her hips back and forth, nearly chipping my tooth on her pelvis!
“Oh my god, don’t stop, fuck, fuck yes, oh, oh, oh!!” she yelped as I built my rhythm ever faster, sucking her clit harder than ever, taking it in my mouth, licking it firmly. Suddenly her breathing changed again, now she was almost panting as she writhed around to my every touch.
“Keep going! Keep going, I’m going to cum. Fuck, fuck, oh my fucking god, I'm going to CUM!” she screamed.
I wasn’t going to stop and by now my whole hand and face were soaked with her juices as I could feel her orgasm building. Her body tensed and just as she was on the point of release I slid my little finger into her asshole. This sent her into new heights of passion.
“Ahh fuck yes! Yes! Yes!” she screamed as the walls of her pussy clamped down on my fingers and a flood of boiling hot cum shot through her tight hole. Despite her cumming, I didn’t stop, I kept my fingers pounding in and out of her cunt with my finger up her ass and clit in my mouth. Less than a minute later she was bucking once more.
“Fuck I'm cumming, I'm cumming again! Fuuuck YES,” she hollered as another full-body orgasm ripped through her, clasping my fingers tighter than ever inside her, and squeezing my head tight between her thighs.
As her orgasm subsided I eased my fingers from her holes and looked up to see her drenched in sweat and shaking. I moved from between her legs to kiss her deeply on the mouth, sharing her delicious juices with her and holding her tight until she stopped shaking.
As she regained her breath she said, “I’ve never cum like that and never more than once, you drive me crazy.”
“Don’t think we’re done, I have plenty of plans for us yet!” I responded with a wicked smile.
“I like the sound of that,” she whispered, reaching for my now-hardening cock once more.
Lying there with her stroking my dick it only took a couple of minutes for me to be at full erection once again. “Now I so, so want to fuck you,” I told her.
“Do you have a condom, because I don’t,” she replied.
I got up from the bed and went to my jeans, delighted that I’d chosen to bring condoms on a first date for once. Once protected I returned to her and pulled her towards the edge of the bed, aiming the tip of my cock for her pussy. I carefully began pressing ahead and heard a sharp intake of breath as my bulbous head began to part her lips.
“Slowly please,” Maggie begged as the first couple of inches entered her. I paused as she shifted under me, then slowly started to withdraw, then pushed in a little further.
“Ugh, ugh,” she moaned as her pussy stretched around my pulsating dick. Gently I pulled back and then in further, deeper than ever. Honestly, sliding into her pussy was more like sliding into an asshole, it was so tight. As I pushed deeper I rocked back and forth, pulling almost all the way out before slipping further into her tight passage.
With a little more than half my dick inside her, it felt I couldn’t go any further and a pained look came across her face. I grabbed her legs and put them on my shoulders, changing the angle of attack and pushed harder. Slowly her cunt stretched, allowing me to slip inside. A few moments later my balls were brushing against her anus as she had my full length inside her.
Each time I withdrew she exhaled a soft moan and with each thrust inside she grunted and inhaled sharply. Soon the look of pain eased into one of pleasure as she relaxed to accept my entire cock. Now I could begin to fuck her properly, so I picked up the pace - marvelling at the looks of passion written all over her face. With the condom on and having already cum, I knew I was going to last a while.
“Oh yes, fuck me, please. Your cock feels so good, fuck me hard!” she told me.
Picking up the pace, I started slamming in and out of her with her bucking her hips in rhythm. Finally, I pushed her legs further back and was hammering in and out of her tight slit when I felt my dick hit something firm.
“OW, fuck that hurt!” Maggie screamed, “I think you just hit my cervix!”
I immediately stopped and pulled out as she caught her breath, beads of sweat dripping from both of us. “I’m sorry, I never meant to hurt you,” I said apologetically.
“It’s okay, I know you didn’t, maybe we should try doggy style - I’ve always wanted to try that.”
I didn’t need to be asked twice! Positioning her on all fours where we could both see our reflections in her dressing table mirror, I spread her legs and started pushing my cock back inside her. Now she was relaxed I slid in much more easily and the view was incredible. With each thrust her tits swayed forward and watching her face in the mirror was a dream come true. Not wanting to hurt her again I gently fucked her from behind, grabbing her hips to make sure I didn’t go too deep.
Back and forth, back and forth we rode in unison, building up a wonderful pace. Soon her breathing changed again and I knew an orgasm was building. Suddenly I saw her reach between her thighs and start rubbing her clit as I pounded her tight wet pussy. I glanced away from the mirror to look at her ass and saw her anus opening and closing in time with each thrust, almost inviting me to touch it. I got a load of saliva and started circling her asshole with my thumb. Immediately her head rocked up and looked me in the eyes via the mirror. I was sure she was going to tell me to stop but instead she just said, “That feels so good.”
Encouraged now more than ever I slipped my thumb right past her sphincter and into her butt. Working my thumb in time with my cock, I could feel her getting ready to cum. I sped up, fucking her harder and harder as my thumb went in and out of her ass.
“Ugh, ugh, god I’m close - please don’t stop,” she said as I kept pounding away. Then it hit, her whole body started to spasm as a wave of pleasure coursed through her.
“Fuck yes! Oh god, yes, yes, yes yeeesss!” she screamed as her already tight pussy clenched down even harder on my cock. Not wanting her pleasure to end, I kept on fucking her and thumbing her asshole.
“Yeeesss! Yeeesss! Yeeesss!” she screamed again as I continued driving into her as spasm after spasm ripped through her body and a tidal wave of hot cum gushed around my cock and began leaking down her thighs. Unable to hold herself up anymore, she dropped onto the bed causing my thumb to pop out of her anus and me to collapse on top of her, my dick still deep inside her.
All I could hear was her panting and I felt her body shaking with pleasure. Even the slightest movement from me caused her to twitch again. So I just lay there, our bodies glistening with sweat, pressing hard against each other.
Gradually her breathing returned to normal and her muscles stopped spasming as her orgasm subsided.
“Sounds like you enjoyed that,” I whispered into her ear.
“I did, but you didn’t cum. I don’t think I can take anymore, my pussy is so sensitive.”
“That’s okay, as long as you enjoyed it, that’s all that matters,” I said.
“But I want to make you cum.”
I told her I had an idea and grabbed a pillow from the top of the bed, I asked her to lift her hips and put the pillow underneath her. I opened her legs then spread her ass cheeks and began to lick her asshole tenderly. Initially, she flinched at the new sensation of my warm tongue circling her butthole pushing into its warmth.
“Fuck, that feels good, but I’ve never done anal before,” she whispered between moans of pleasure from my tongue action.
“It’s fine,” I assured her. “You’re already relaxed and as long as you stay calm it will feel amazing. Trust me.”
I spat a ton of saliva onto her ass and began working it inside, first with one finger, then two and finally three. After her orgasms, her anus stretched much more easily than her pussy had. When I was sure she was ready I eased my dick next to her asshole and pressed gently into her. Almost immediately the head slipped straight inside.
“Wow!” she gasped with a cock in her ass for the first time. “My god, that feels big!”
I stopped and allowed her to expand then slowly began withdrawing, watching until her anus was wide open around the fattest part of my tip, then pushed inside. Inch by inch, thrust by thrust, my dick worked its way into virgin territory.
“Ow, gently, gently,” she urged as I slowed so she could accept my full length.
Once she was comfortable I started to fuck her, gradually picking up the pace as her anus contracted around my dick. The sound of my thighs slapping against her butt was intoxicating as was the mix of pleasure and pain crossing her face. Soon she was fully into the swing of things and began pushing back, urging me to fuck her deeper.
Before long I felt my balls tightening once again and knew I wasn’t going to last much longer. I slapped her butt and said, “I’m going to cum in your ass any second!”
“Wait, don’t cum yet,” she screamed as I saw her hand head towards the pillow supporting her hips. I knew she was rubbing her clit trying to cum again. I had to slow my pace to hold back my orgasm and then it started. Her breathing changed, her hips started rocking once again and I could tell we were both about to cum.
“Fuuuck, yeeesss, I”m going to cum now. Cum in my ass,” she panted.
This was all I needed, and I picked up the pace once again, slamming into her virgin ass as hard as I could.
My balls were so tight they hurt as my cock started twitching and I screamed aloud as spurt after spurt of cum fired deep into her asshole. Soaked in sweat, I collapsed on top of her, my cock still nestled inside her anus.
“That was incredible,” I muttered in between heavy breaths.
“A-fucking-mazing,” she gasped.
As my dick became flaccid it slid out of her ass and I rolled off Maggie. I removed the condom and put my arms around her, spooning as we caught our breath. Within moments she was sound asleep, tight in my embrace. I fell asleep savouring the rich aroma of passion in the air.
That was the first night Maggie and I were together. Since then, she has become a much more sexual being and has grown to love and embrace her desires. We've had plenty of memorable times together.
Oceana
- 12.04.2022
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