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Nurse Leslie – The Begining

Category: Anal Sex
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As you will no doubt have read “Nurse Leslie — First Fist”, you will have had a peek into my life with my sexy little vixen. Let me back track a bit here and start at the beginning. Leslie is a lovely woman, ten years my senior and unable to have children. This came as somewhat of a disappointment to me when I discovered it after we had been dating about two weeks. I had always wanted kids — but, man, she was so damn sexy. Her whole body just oozed sexual excitement.

Standing only five foot four in stocking feet her curvaceous body was taut yet supple. The things, though, that drove me to her were her gently smiling blue eyes and caring demeanor. From our first discussion while on a singles adventure canoeing trip I was enamored. Her caring, attentive, intelligent way had me hooked, not to mention her looks. She was different; she really cared about what you had to say, not just with me, but with others in our group as well. It had been a while since I had met a woman that I could have an intelligent discussion with and who brought out the best in people, as she did with our group. Leslie was a lady, not one vulgar word or action. I am convinced that the trip was socially enhanced by this caring woman.

She caught me staring at her lovely face on more than one occasion and her eyes twinkled back at me. I knew then that we shared a mutual attraction. She was very different looking from the women I usually dated. Leslie was short, curvaceous yet athletic, with short brown hair and big brown eyes. The women I was usually attracted to were tall, skinny blondes with big breasts and tiny asses with legs that went all the up to heaven. But I found myself not even reflecting on this and solely focused on lovely Leslie. I was so surprised to find that she was not already taken, and awkwardly broached the subject, which was entirely unlike my outgoing, carefree personality. Leslie also admitted later that she felt awkward asking me the same thing. At thirty-five I am six foot, athletic and not entirely unhandsome, and somewhat successful in business. She asked me straight out where my blonde, long legged girlfriend was. Boy, did she have me pegged. I answered quite truthfully. I replied that I was unattached and taking a break from the never-ending search. Her reply caught me off guard when she said, “That’s always when you find the perfect person.”

After the trip I spend hours relentlessly pursuing her phone number from the tour company because I stupidly, head-bangingly, had not had the courage to swap phone numbers with this lovely, out-of-my-league woman who did not fit my stereotypical type.

You see, I wanted my Leatherman all-in-one tool back, which I was sure I had lent her and not retrieved. It was important to me, essential, you see. Ok, I admit it; I really wanted to see her again. When I called her she sounded on the phone like she was expecting it, and the blood was rushing to my head. I felt like a randy teenager again. After a wonderful conversation she asked me for dinner which I answered yes without a thought. After taking down her address, which I already had from the blond bimbo at the tour company, I planned the perfect, gentlemanly visit.

I bought a pleasant arrangement of flowers and a nice, but not too expensive Chardonnay and knocked on her door at precisely the appointed time. Never keep a woman waiting, my mother always said. And Leslie was quite the woman. She answered the door in — no, not a see though negligee and fuck-me pumps, but a lovely, but simple three quarter length dress, buttoned all the way up the front – complete with bunny slippers. I did not laugh outwardly, her eyes were shining too brightly. Lesley ushered me in the door and we had a delightful dinner together.

When do we get to the sex you ask? Well, it took three wonderful dinners together where we took turns cooking. You see, I am not completely out of my league with holding the ladle, as my many years prior in the high-end restaurant kitchen had taught me. The office life held me now, and I was none the better for it. Anyway, our first sexual encounter was unexpectedly awkward at first.

I groped, and she pushed back. “Are you sure this is what you want?” She enquired.

“Lesley, I have never been more sure of anything in my life,” I answered truthfully.

“Then take me fully,” she replied.

And I did. More fully than I had taken anyone in my life. I savored each kiss, each caress, and each passionate touch. She was one with me as we made love, neither of us uttering a word.

When we finished our marathon love making session, each too afraid to break the moment, we basked in our togetherness. It was a feeling I had not felt in long time. I spent the next three heart-tugging days away from her, wallowing in my decision. When I called her back she practically cried at hearing my voice, and I nearly broke down too. I needed her, I wanted her, more badly I think, than she needed me.

Ok, ok I’m getting to it — the raw sex. But Leslie was more than raw sex. She was passion itself. The very definition of the word. Our next dates involved long sensuous massages and long, deep discussions of feelings and desires. We each found long buried passions and fantasies. As I said, the subject of children came up, and our age difference and I made my decision. This wonderful woman, so full of energy and youthfulness, consumed me. Ten years my senior, but equal in every way, had me straight through my heart and soul. I told her truthfully my concerns and Leslie cried for me, understanding and caringly held me tightly.

Then the passion resumed, like make up sex. I wanted this sexy woman like no one I had had before. She was raw sex, an animal who seemed to discover new heights each time we made love. Each time was more passionate than the last. It seemed to me like I was able to bring her to her first orgasm by sucking on her tender clit. Our sex still consisted of delicate and non-vulgar words. But she surprised me at each turn. When I made love to her she reached back and massaged two fingers in beside my prick, then forced her wet, sticky finger in my mouth after we came together. My tongue urged her sucked fingers back into her own mouth as we shared our kiss and she greedily lapped it up.

Two months into our relationship I delicately broached the subject of anal sex. I had been sliding a small finger delicately up her anus as I sucked on her pussy and she had writhed and moaned at the anal attention. I asked politely if I may put my cock in her bum. She stared at me with a raw look in he eyes and said “will you be gentle?”

“Oh my God Leslie, I will be so gentle and loving. The last thing I want to do is hurt you.”

The first time she got on her knees and offered her beautiful bubble shaped ass to me. As her ass was thoroughly lubricated from our lovemaking I slowly, delicately fed my hardness into her and she moaned sexily at the intrusion. Inch by inch I penetrated her lovely rectum as she rubbed fervently at her distended clit. It felt tighter than I had ever had any ass before. When I hid bottom, with my pubic hair against her cheeks, I advanced back. Looking down I discovered the shit she had saved deposited on my hard cock. I pulled out and embarrassedly ran to the bathroom where I washed it off.

When I got back to bed she asked what was wrong. I didn’t have the heart to tell her of the disgusting mess she had deposited. I knew she wanted more, but I was turned off at the time.

Three days later, on the Friday night after a sumptuous dinner and drinks we fell into our usual love making session, complete with sensual massage, when Leslie asked that I “fuck her ass again.” Well, this blew me away. This delicate, little flower uttering such crude words. I gasped, unsure what to say next.

“Pardon me?” I exclaimed, “I mean, I heard what you said, I just can’t believe those words came out of your mouth.”

“I’m cleaned out this time,” she continued.

“Oh, Leslie, I want your ass so bad. I’ve been dreaming of doing you like that.”

“It’s ok Jack. You can say the words. It actually gets me excited.”

“But you’re so prim and proper…”

“And downright nasty at the right times,” she cut in. “Now, are you going to stick your throbbing cock in my ass or what?”

“Leslie, I’m going to stretch that cute little rosebud of yours and fuck your beautiful ass silly.”

“Ooo,” she cooed, as she caressed my cock, “look how hard you’ve suddenly become. Let me get it lubed up before you fill my anus.”

She reached back into her beside table drawer and pulled out a large bottle of lube. My brow arched in surprise when I saw it. What other revelations did she have for me?

“I’m not new to ass stretching Jack. I just love the feel of my hole being stretched while I bring myself to orgasm.”

She copiously lubed my cock in the slippery liquid and massaged my swollen prick and balls with her talented hand. My body temperature instantly elevated several degrees as she kneaded my pulsing six inch member.

“Holy fuck Leslie. You better not do that too much or I won’t be able to shoot my load in your ass.”

“Oh… I want you to come my ass.” She said as she took her hand off my cock and lubricated her anus with her slippery fingers.

She pushed me onto my back and straddled my hips then guided my cock inside her tender rose bud. The feeling was incredible as her anus slowly expanded to accept my swollen member. Leslie pushed down with shear delight on her face with her eyes lightly closed. I massaged her gorgeous 35D breasts and large areolas as I watch her rise up slightly. My cock was tugging at her tender orifice as she alternately sat deeper, forcing more erection inside, and then pulled up slightly.

The blood was coursing through me and my skin was on fire, all the hairs on my body raised.

As she fully seated her tight sphincter on my cock we groaned in unison. Her eyes bolted open and she stared into mine.

“Fuck that’s so good. I love the way you fill me.”

“Oh Leslie, you’re ass is so tight.”

“Oh ya… how about this?” And she clenched her ass muscle as she leaned forward, my cock sliding slowly out a couple of inches.

“Holy fuck that’s good. I won’t be able to hold out much longer. Fuck my cock with your tight ass Leslie. Make me come inside you.”

She moved back and forth over me, pistoning my cock in and out of her ass. She licked three fingers lewdly and thrust them to her throbbing clit. I tried to hold out as long as I could, savoring the incredible feeling. I wanted us to come together, sharing our sinful bliss. My orgasm boiled inside me, wanting to rush out like a freight train.

I could sense her impending orgasm as her breathing increased rapidly and her head rolled back slightly.

“Come with me now Jack… fill my ass with your hot liquid!” she screamed.

I came and exploded and erupted violently inside her hot anus and she bucked wildly above me, orgasming forcefully. Her orgasm made her every muscle pulse and contract on my squirting member. The blood rushed from my brain and I screamed, “Oh Leslie! Arghhg… I love you!”

She didn’t even hear me as her spasms wracked through her, my cock seated deeply in her ass.

She began screaming incoherently and continued rubbing her clit forcefully. Suddenly I felt the sheets under my ass get wet and realized that she had ejaculated liquid from her pussy over us both. We were soaked. Slowly her contractions abated and she slowly lifted off my cock.

Unbelievably my cock was still somewhat hard. She shoved three fingers in her soaking twat then pressed them into my mouth. As she slid her slippery pussy against my cock she lowered her mouth to mine. We kissed passionately and sucked at her drenched fingers together.

Finally she started to recover and gazed into my eyes. “That… was incredible… I’ve never come so hard in my life.”

“Neither have I,” I replied.

“Did you say what I think you said, or I should say, screamed?”

“I love you Leslie. I love you so much.” I admitted for the first time to her.

“Oh God Jack… I love you too.” She collapsed on me and sobbed tears of joy into my neck.

I hugged her tightly and repeated that I loved her. And her body wracked with momentary convulsions as she cried and continued orgasming.

Chapter two

When we both calmed down enough to breathe properly she laid beside me, my arm around her shoulders. With her fingers entwined in mine we began our discussion.

“Jack, can I keep you?”

“Leslie, it is me who should be asking that question. I have honestly never met anyone as passionate, sexy, and gorgeous as you. I want this to last forever.”

“You’re not going to run off with some bimbo?”

“Been there, done that… now I realize that it’s you I’ve been searching for.”

“Me too. You know at forty-five I don’t get many dates. And I’m kind of selective. Jack, you know I’m ten years older than you.”

“I can’t believe how you wouldn’t have a line up of men waiting for you. And yes I am aware of our age difference, but only because you told me your age. You are so vibrant and youthful.”

“And you are a kid at heart. That’s one of the things I love about you.”

I smiled, and she gazed over at me thoughtfully.

“I mentioned kids, didn’t I?”

“Lesley, I love kids. But that doesn’t mean I can’t still enjoy them. My brother has kids and your sister has young kids. Can’t we offer to baby-sit and stuff? Then we don’t have to deal with all the parenting issues I hear so much about.”

“Oh Jack, I really love you.”

“Me too Leslie, I love you more than words can say.”

“Um, Leslie.. are you aware that we are laying on soaking wet sheets?”

“Ah… ya. I was kind of wondering about that…”

“You soaked us Leslie. Your orgasm was one wet one.”

“I did that? That’s never happened before.”

“Really? You didn’t know you’re a squirter?”

“A squirter? No, I didn’t. But I’ve never orgasmed so hard in my life.” Her hand brushed up against my flaccid cock and I felt it immediately twitch.

“Again?” I exclaimed, “fuck Leslie, you are one hot little number.”

“I can’t help myself Jack. You really get me going.”

After a long pause I tentatively said, “I’m curious; you said you really like to stretch your tight little hole. What do you use to stretch it with?”

The silence was deafening.

Leslie breathed deeply and admitted, “Jack, I’m sorry I’ve been secretive with you, but I have a collection.”

“A collection of what?”

“Now don’t laugh at me Jack, be nice. Look in my drawer under the bed.”

We got off the wet sheets and I bent down to slide the drawer open. To my surprise she had a large collection of vibrators and dildos assorted neatly on a towel.

My eyes went wide and I salivated at seeing the fine collection.

“Lesley, this looks like the same assortment that I have,” I admitted, without thinking.

“You have?”

I blushed deeply.

“Do you use these on your bimbos?”

“No Leslie, I don’t. No one knows about my collection.”

“You mean…” she stammered.

“Yes Leslie. You’re not the only one with a red-hot little ass.”

“Oh God Jack, you mean it?” She exclaimed. And I blushed even more deeply. I swallowed.

“Yes Leslie, I love anal too. There, I said it. Are you going to dump me now?

“That’s so sexy.” She paused, “You’re not bi, are you?”

“Not in the least. But I do love a good prostate massage.” I ventured, tentatively.

“Wow,” she pondered. “So you know how I feel?” As we stood there beside her bed her fingers ventured into my ass delicately.

“Yes, and I want you to stretch my ass too.”

“Really?” as she pressed her fingers into my wet anus. My cock twitched convulsively, as did my sphincter. “Jack, I want your ass. I need your cute little perfectly formed ass.”

“Ok, but can we change the sheets first?”

“No. First I want you to stick this butt plug up my rear.” She reached down into her toy chest and retrieved a medium sized butt plug.

“I wanted to wear this before you came over tonight. But I also wanted my asshole to be extra tight for you.”

“And it was. I have never felt a finer little asshole,” I said as she placed the plug in my hand. I reached over to the lube and squirted a small dollop on my hand. She was still well lubricated, I discovered, as I reached around to her behind and slid my fingers into her crack.

Leslie bent over the bed and stuck her butt out for me.

“Push it into my hole Jack. Stretch me out,” she meowed, as she gazed back at me over her shoulder.

I tenderly placed the tip against her rosebud and pushed gently. She groaned deeply as the widening intruder stretched her cute asshole. She grinded her hips back at me the widest part of the plug suddenly seated fully in her rear.

“Ahhg…” I love that. How does it look Jack?”

“Fucking sexy,” I whispered as I twisted it slightly back and forth, causing Leslies eyes to close in pleasure. I tugged at it delicately, and her sphincter pulled it back in greedily.

“Mmm that feels so good. But I want to see your sexy butt stretched too. Help me get this sheet changed.”

She walked awkwardly to her closet and retrieved a clean set of sheets. From the opposite side of the bed she tore the bottom sheet off and the protective undersheet and balled them up and placed them in her hamper. Then she moved back to the closet and bent over, exposing her plugged ass to me , as she reached down to the lowest shelf.

I gulped involuntarily at the sight and my eyes burned like laser to her sexy behind.

She caught me staring. “I thought you might like that view,” Leslie teased.

“Oh yeah… I can’t wait to run my hands all over you.”

What she brought back from the shelf surprised me again. She grasped two ends of the black latex sheet and billowed the other side out to me.

I caught a part of it and exclaimed quietly, “Don’t tell me you like latex too?”

“You mean ‘too’ in like, all the other nasty things I like; or ‘too’ in, you like it too?”

“I fucking love it.”

“I had a feeling you might,” she winked at me.

“And what led you to believe that?”

“Just call it woman’s intuition.”

“Wait to you see my latex collection,” I whispered as I gathered the smooth, cold sheet and began tucking it in.

“I can’t wait…” Leslie spoke softly back seductively, as she tucked in her side.

“Let me see your cute plugged little ass again,” I whispered as we climbed on the bed to each other.

She wiggled her hips over to face away from me, bending around to stare into my eyes the entire time.

“Want to fuck my tight ass again?” she squirmed at me.

“Fuck ya, I want your ass. But all this anal talk has got my ass pretty itchy too.”

“Let me see your tight little butt.” Leslie sidled her ass back, pushed me back on the bed and straddled my face, her wet pussy an inch from my mouth.

“You really like to be on top, don’t you?”

“Ya, I do. Do you have a problem with that?

“Not at all,” I moaned, and licked devouringly at her descending pussy.

She pulled up my knees and parted my buns gently, probing with her wet fingers at my twitching orifice. Her hand grasped backward for the pump of lube. She found it quickly and pumped a generous dollop into her hand. Leslie wetly coated my anal opening, balls and cock, she then press two fingers against my puckered anus.

I moaned deeply as she caressed my sphincter and the area between my balls and anus.

“Feels good, does it?” she praised.

I licked her dripping pussy and clit enthusiastically and reached around to pull delicately at her anal plug.

“I’ll take that as a ‘yes’,” she moaned.

“How about this?” as she opened my ass with her fingers. I involuntarily pushed my ass back and she heaved a sigh, “two fingers so easily?”

I moaned into her wetness, she spread my anus wider, stretching my sphincter delightfully. The cold latex sheet felt delicious under my body as Leslie pried my eager ass open.

“Believe me; I can fit more than just two fingers.”

“Oooo… Fuck. That’s so hot. Do you want more?”

“Oh yes Leslie, Stretch me open.”

She tenderly pressed two fingers from her other hand in with the two already in me.

“Can I put a vibrator in your ass Jack?”

“Yes. Please. My ass is itching to be filled.”

Her fingers suddenly departed from my sphincter, leaving my craving starved. She bent down to the drawer and pulled out a small vibrating dildo. She leaned back on her haunches and showed me the dildo.

“That’s it? Leslie, I need something bigger than that tiny little thing.”

“Really?” she bent down again and showed me a much larger pink vibrator with a girth of at least one and half inches. “How about this?” she teased.

“That’s better. I have that same one at home and it’s my favorite. I am cleaned out, by the way.”

“Are you now?” she stretched back and winked at me.

“I love this toy too. Let’s see how easily I can slide it in you, shall we?” as she turned on the vibrator and pressed it to my hole.

“Mmm… that feels so good. Push it in me.” I felt my wet pucker expand to accept the velvety soft vibrator. The realistic veins and contours rippled against my pulsing sphincter.

“Damn that looks sexy Jack. Your ass is just swallowing it,” Leslie purred as she twisted and pushed it deeper inside me.

“That’s it Leslie. Fill my ass, stretch it good. Fuck my ass with that big toy. Ghmmm. Turn it up and fuck me deep.” I pulled her dripping pussy down to my mouth and slurped hungrily at her open cunt. My fingers found her plug deeply seated in her ass and I pulled at it, stretching her asshole out.

“Oh FUCK Jack. That’s so good. You’ve got me so wet. I love fucking your sweet ass, it makes me so horny.” Leslie excitedly started thrusting my dildo in and out of my stretched ass.

“Yeah, yeah, YES. Pull at my plug. Pull it all the way out and push it back in. Stretch my ass while I stretch yours. Oh Jack, this is so good. I never dreamed I find anyone so anal.” Her lips grasped for my throbbing prick and sucked it deeply into her mouth as she plugged my ass full.

I was unable to respond as we each slurped lustfully at each other. Our moans grew loader and more urgent as our orgasms approached. I could feel Leslie’s legs begin to tremble as my cock grew in her hungry mouth.

“Mmmghh,” Leslie mumbled loudly as her body started to shake uncontrollably, pouring her ejaculate into my mouth.

“MMMghh,” I groaned and my cock erupted forcefully in her slurping mouth. My second orgasm in less than half an hour I knew was not as copious as the first, but it was definitely more powerful. My entire body tensed forcefully as I came. I shuddered repeatedly all over and my prick became overly sensitive. Somehow Leslie knew this and released my still twitching cock from her mouth and gently slowed pounding my ass with the huge dildo.

Her body also convulsed as her orgasm racked through her, her legs involuntarily shaking. She dropped off to the side of me, her fingers reached to her soaked cunt and parted her labia and probed her sodden depths. I pulled gently at her butt plug and it popped out. Her ass was really stretched as I stared at her gaping, twitching hole. Fuck, I wished I was hard enough to fuck her ass again.

Leslie let the still vibrating dildo slide out of my ass and she pressed the fingers from her other hand inside my gape. Swirling her fingers inside me, she mewed and writhed. With our bodies opposite we squirmed against each others heated skin. Her legs against my chest, her heavy breasts against my thighs, her nipples caressed the hair on my legs.

“So good Jack. You feel so good.” She sighed between breaths. Leslie slid around and looked deeply into my eyes, her caring and love shining through.

Her eyes then twinkled with lust as she whispered, “I can’t wait to fuck your ass with my strap-on.”

My eyes opened and went wide at her statement.

“Would you like that Jack? Do you want me to fuck your ass with a strap-on?” She purred.

“Oh Leslie, yes. I’ve fantasized about that. But only if I can play with your beautiful breasts and your ass is plugged too. I love watching you squirm.”

“Fuck yeah, that sounds like a great plan. Oh, I love you Jack. You are so perfect for me.”

“I love you Leslie. I think this is going to be a long and beautiful relationship.”

“Me too, my little anal match,” she giggled.

I held her tightly as we basked in each others togetherness.

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