Doing Jessica and a BIG Surprise

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Doing Jessica and Getting a BIG Surprise!

She was really good looking. Her bikini barely covered her amazing big tits and drop-dead ass. Her legs were long, lean and sexy as hell. She was sunning by the pool, her skin slick with oil and sweat.

Being the perv I am I'd been watching her through my Ray-Bans. It was becoming difficult trying to hide my engorging cock. It was becoming the whole tent-pole-in-my-bathing-suit thing. Apparently I failed, because as she turned over from her front to sun her back she noticed me, looked surprised for a second as her eyes went south to my growing bulge, then gave me a big smile and wink.

Holy shit! She caught me perving on her. I turned away quickly, blushing under my sweaty tan.

This all happened many years ago, before I was married. At that time I worked for a firm that conducted conferences around the US. I had the good fortune of being able to travel to posh resort hotels very often.

Being a young, horny 20-something year old I was the guy who's picture you saw if you looked up "single and ready to mingle" in the dictionary. At each conference I flirted with, teased and seduced as many willing women as humanly possible.

Well, to be accurate I should say 'tried to seduce' as my track record was not stellar in the whole seducing willing women department.

Being the advance lead for each conference it was my responsibility to spend several days in the hotel prior to and then during each conference. I loved it. It was what I liked to call a target-rich environment.

This conference had started out like any other, but would change quickly to be one of the most amazing sexual encounters of my life.

I was in Scottsdale AZ, in a hotel that had a huge spectacular pool. I was sunning my hot bod, displaying my skin-tight, ultra-thin and ultra-tight white trunks (and junk underneath) to advertise to any and all prospective one-night stands, er, I mean women.

I'd picked this particular lounge because of the hot blonde a couple seats over. She looked to be in her late 30s or perhaps very early 40s, but she clearly kept herself toned, fit and sexy as hell.

I'd placed myself near enough to ogle her behind the cover of my shades, yet far enough that I didn't seem like a pervert and chase her away.

Damn! She's so f-n hot!

She was tall, even without the sky-high mules that made me want to kiss and worship her feet and red polished toenails each time she walked by. A devastatingly gorgeous blonde, she had all the guys doing double-takes as they suddenly slowed to walk by her lounger, staring unabashedly at her womanly perfection.

I went back to staring at her. I had never seen a bikini so small! It barely covered her naughty bits, leaving a LOT to feast my sex-crazed eyes on. She had a bottom G string and a top that covered her areolas and left the rest of her stunning boobs exposed to the sun, and my lusting eyes.

But dang! She seemed to be enjoying the attention of the men stumbling by. She flaunted her devastating body and breasts with a nonchalant attitude that screamed I'm hot and I know it.

The sun was lower in the sky, and I had the sinking feeling she'd be leaving soon. If I ever wanted to do something to try to flirt with her now was the time!

Feeling anxious yet brazen, I lurched out of my chair, quick-stepped to the bar and asked the bartender to mix me another of whatever she was drinking. When ready, I brought her the drink.

Approaching, I managed an "ahem" to arouse her attention. She turned over and sat up, looking at me with a confused expression and a raised eyebrow. I tried to yank my lusting eyes away from the beads of sweat dripping down her mammaries and into the crevice of her gorgeous cleavage.

With a flash of my best dazzle-em smile I gently offered her the drink.

"I, er, got this for you." I stuttered.

Her tiny bikini top left almost nothing to my imagination, her boobs were massive and magnificent! Up close, her wide hips and long, long oiled legs were even more stunning! She had to be a model. My heart raced as the smell of her pretty perfume wafted, mixing with the scent of her Coppertone and sexy sweat.

Mmmmm, she's an absolute 10.

"Why, thank you very much for the drink." She beamed at me with a dazzling smile, taking the proffered drink with her long red manicured nails. I casually noticed the huge rock of a wedding ring on her finger, but that fazed me not at all. Married or not they were all a target for my lustful desire.

"You looked hot, so I thought you might need a cool down." I grined, fully intending the double entendre.

"Yes, I'm definitely hot!" She laughed, winking at me. "Hi, I'm Jessica. Would you care to sit down?"

"Ummm, sure!" I said, wondering how a guy like me who didn't have a date until his Junior year of high school was suddenly talking to a stunning woman like her. "My name's Tom, but friends call me Tommie."

"It's a pleasure to meet you Tommie," she said with a grin as we shook hands.

She started chatting. She told me she was here on vacation and noticed me earlier, wondering about my smooth body, tight abs and broad shoulders. I explained I worked out, and the conversation then flowed like water.

After a half hour and several more drinks she leaned over to me, touching my arm gently and whispering. "I think you're very charming, and I like you. A lot." She looked down, apparently trying to resolve an inner conflict. Her mind apparently made up, she looked me in the eyes. "I've a very personal question, so if you don't want to answer that's fine."

"Sure, go ahead." I said, intrigued and wondering where this was going.

"I like you, and I think from our conversation you like me, is that true?"

"Uhhh, well, yes, of course!" I blurted out, surprised by her forward manner.

"There's no gentle way to say this, so I'm just going to put it out there," she whispered, taking my hand in hers and looking into my eyes. "Are you into swinging? You know, with a couple?"

I was so clueless at that time of my life that I thought she meant on a swing, and being embarrassed and oblivious I spluttered yes before I even knew what I was agreeing to.

She looked around to see if anyone was in earshot. She leaned closer, moving her hand to my knee as she whispered in my ear, "My husband and I are into the lifestyle. He enjoys watching me with young, hot studs. Studs just like you. Would you be interested in coming upstairs and having some fun with us?" She batted her long, dark lashes while gently stroking my upper thigh with her nails.

Stunned, and starting to get the picture of what she was talking about I nodded, agreeing to her request without thinking. I had never, ever had a stunning woman ask me to do anything remotely like this.

Smiling with a sexy little laugh she collected her things and together we walked up to her room. Following behind her as she led the way my cock grew rock hard. I stared at her heart-shaped ass and sexy legs as she on-purpose wiggled her butt with exaggerated steps.

At the penthouse floor she opened a door to a large suite. Picture windows offered stunning views of the pool complex as the late afternoon sun descended over Camelback Mountain.

Out of the bedroom next to the living room an older but in-shape and still good looking man sauntered out. I guessed he was in his late 40s or early 50s. He smiled as he offered me his hand. He was dressed in nothing but a skin-tight black Speedo swim suit, his rod clearly visible tucked against his leg. His hair was slightly gray at the temples, but not too far gone to be called 'old.' Masculine and mature was how I'd categorize him. I instantly lost my hard on.

"Hi, I'm Ted." He said in a deep, warm voice. He smiled while shaking my hand with a vice grip. "Come on in, it's great to have you!" He added with a wink.

Shocked and feeling like I should run, yet at the same time feeling like I must stay, I slowly entered the room. My insides became watery as nervous energy raced through my heart.

He gestured toward a large sofa. "Have a seat. Can we offer you a drink?" He asked as I sat on the couch. Not really knowing what to do and feeling slightly nauseous from the strangeness of the situation I nodded.

Jessica strode to the wet bar in her mules, and my attention briefly wandered as I focused yet again on her sexy legs and the way her butt swayed as she walked. Ted must have noticed as he smiled at me. Patting my back he stated, "Hell of a view, eh young man? And I didn't catch your name."

"Oh where are my manners?" Jessica pronounced at the bar as she mixed the drinks, "Ted, I'd like you to meet Tommie. Tommie, this is my husband Ted." Ted sat on a chair facing the couch opposite me. He leaned back while opening his legs. Was it me or was his cock growing down his Speedos? I yanked my eyes back up to his face, but his grin told me he'd caught me checking out his package. I blushed a dark crimson, what the hell was I doing looking at him and not her!

Ted began to explain why they decided to explore the lifestyle, why they finally tried and loved swinging, and why he found it so sexy to watch his beautiful, sexy wife get taken by young, hot studs.

Jessica glided up, her butt and hips sashaying as she handed us our drinks. Feeling super nervous I pretty much chugged what turned out to be a very strong gin and tonic.

She sat on Ted's lap and talked about how enjoyable the two of them found swinging. As she talked about how much she enjoyed having sex with other men my cock grew and before I knew it I was rock hard again.

I was feeling more relaxed as the Gin did its work. Noticing I was empty already she mixed another round as Ted explained how they used these vacations to meet young, hung, willing studs.

Jessica turned on a radio to a Dance/Trance station and handed me a drink.

Stepping back she asked with a naughty grin, "Would you like a little show?"

"Umm, yeah, I guess." I stuttered not very brilliantly.

She smiled and gave us a slow, sexy striptease to the beat of the song. Ignoring Ted she faced me, playing with the straps of her top and bikini bottoms as he teased me by revealing more and more skin.

Her sexy bump and grind became more erotic as she teased me by removing her top, using her hands to hide her areola and nipples. She swung her butt and hips, tossed her hair, and bent over to provide me with an almost complete view of her tits and ass, hiding only her nipples with fingers perfectly placed.

My rod was hurting, crunched in my trunks and I had to surreptitiously move it as I grew harder and harder. She grinned, noting the effect she was having on me.

With sensuous movements she climbed into my lap, hanging her legs off either side of my legs as she revealed her amazing full breasts in slow motion. With a slutty stare she swayed to the music, rubbing her now naked tits on my chest.

She bent backwards, contorting herself like a gymnast, placing her hands and head on the floor. This gave me an incomparable view of the thin material bunching in her pussy on my lap, giving her a cameltoe and me an even harder erection.

I so badly wanted to touch her, or at least stroke my rod but was embarrassed. Out of the corner of my eye I noticed Ted had removed his Speedos and was stroking his long, rock hard, ridged pole as he watched his wife give me the ultimate lapdance.

She reached for my hands and I helped pull her back up to my lap. Her pretty fingernails stroked ever so gently up and down the bulge in my trunks.

"I think he's almost ready." She slyly said over her shoulder to Ted. Standing she bent over to look me in the eyes.

"Stand up." She commanded.

Not needing further instruction I did as I was told. She reached her fingers in underneath my waistband and eased my tight swimsuit down over my raging, turgid shaft, then down to my ankles.

As she did so, she knelt down, her perfect face and mouth just inches away from my throbbing cock.

"Oh!" she said quietly, "looks like you're having some trouble here with some stiffness, let me see if maybe I can help."

Her soft, pretty hands glided every so gently up and down my swollen member. Precum dripped in an endless flow as my cock twitched to her touch. Slowly she opened her mouth, running he tongue around her lips, and all the while watching my eyes. With aching slowness she brought her now open mouth inch by inch closer to the head of my cock. She paused. Staring me in the eyes with lust she inched her mouth forward and around my swollen cockhead.

When she closed her mouth around my shaft and very slowly starting gliding up and down I thought I was going to pass out. After only a minute of two of her giving me the best blowjob I ever had I realized I was about to cum. Sensing my plight she stopped.

"Ted," she uttered in a lust-filled voice, "the stud is ready."

She stood. Teetering on her high mules she grasped my cock tight and pulled me up by my cock. Wiggling her now naked ass side to side she pulled me by my cock just like a bull being led by a chain. She led me into their bedroom and turned me to face her, my calfs against their kingsize bed.

Without warning she pushed and I fell onto the bed on my back. She crawled up to me and once again slowly lowered her mouth over my raging, hard cock. Near explosion and my head buzzing from the drinks, I could only enjoy her amazing blowjob.

After a few minutes of sucking my cock up, down and around she paused. She moved on her knees to a position where her shaved cunt was directly over my face.

"Lick it." She commanded as she mashed her wet dripping cunt onto my mouth. I did as commanded, licking her juices as I glided up and down her slit, sucking in her essence. I tickled her clit with swift, random movements of my tongue.

She stiffened, grabbing the back of my head with both hands as she squatted her full weight onto my face. I couldn't breath as I continued to love her slit and clit with my tongue. My air started running out, my lungs craving fresh oxygen. If I was going to go, this was one hell of a way to do it!

Nearing asphyxiation I desperately pushed on her legs to try to move her. She finally gave way, lifting her soaked snatch up just enough for me to take big gulps of air.

With raging lust in her eyes she moved down to squat over my straining shaft, never taking her eyes off mine. She reached behind her, held my cock with her perfectly manicured hand and guided it smoothly to rub up, down and around the opening of her dripping love tunnel.

"Are you ready for this, stud?" She asked in a soft voice. After a pause, she inched herself down onto my slippery, thick, pre-cum and saliva coated cock. Her warm, wet cunt stretching to take my manhood.

"Ohhhh! Fuckkkkkk!" She grunted as she bottomed out on my aching tool. Resting a moment she then started slowly moving herself all the way up to the tip of my rigid pole, before pausing, then sliding back down with almost infinite patience, grunting and gasping as I filled her to the hilt again.

"Mmmmm! Fuck, your cock feels SO good buried inside me!" she gasped as she started quickening her pace.

She fucked my hard shaft with long, deep strokes, rising each time to my tip, then burying her cunt all the way back down on my engorged shaft.

I was lost in deep lust, feeling her warm, wet cunt slide up and down my raging cock. In my lust haze I was only dimly aware of her laying her full length on me, then gently but firmly rolling us over so she was now underneath me, me on top, my cock still deep in her wet and willing pussy.

I started pumping into and out of her, moving my shaft faster, deeper, with more urgency in and out of her slurping cunt. Pussy fart noises mixed with the swishing and sloshing as her juices freely ran down her slit. Feeling high I was only dimly aware of her playing with my balls and ass, her fingers providing additional stimulation to our lustful coupling.

Her fingers circled my anus, probing and touching and circling in a most erotic way. I hadn't felt a woman play with my ass and asshole before. In the dim haze of my fucking-brain the distant thought crossed my mind that it felt amazing.

She circled my hole, using the warm juices from her sloppy cunt to lubricate her finger and my anus.

Gently, she pressed her finger into my ass as I slowed my thrusts into her cunt, allowing her to access my now willing sphincter with her finger.

The feeling of fucking her cunt while she fucked my ass with her finger was so intense that I became lost in pure pleasure.

A small bit of my conscious brain began to gradually realize Ted had positioned himself behind and above me, spreading my legs wide. Lost in my fuck-lust I felt something good on my ass. Slowly I realized he was strumming his fingers up and down my ass along with hers.

As my conscious brain swam back up from pure fuck pleasure it dawned on me that Ted was toying with my anus and butt. Shocked at first but unable to stop accepting the intense pleasure of fucking Jessica I relaxed, enjoying this new pleasure eminating from him playing with my ass.

I don't know exactly when it happened, but as I continued to pump into Jessica's slippery, hot hole I could feel Ted's warm, hard cock rubbing up and down my ass crack. His cock was lubricated by his wife's copious juices coating our thighs.

I couldn't stop pumping her. And as his fingers entered and opened my ass and his cock pressed against my brown opening I realized what was going to happen next. He was going to try to fuck my ass with his big, rock hard cock!

I stopped pumping her as he guided his slick cock head against my hole while withdrawing his fingers. I felt the head of his cock rubbing circles against the now slippery entrance to my chocolate tunnel.

"You ready for your big surprise, stud?" Ted whispered in my ear as he leaned down on top of me.

"I'm going to fuck you in your ass while you're fucking my wife. And you're going to love it." He uttered, grunting as he pushed just a bit more of his head deeper into my hole.

"Just accept it. Relax your hole. I promise you you'll grow to love having a big cock buried deep in your butt."

He grunted in my ear again as he pushed just a little more of his swollen cock head further into my sphincter.

It occurred to me the fucking motion of my thrusting into and out of Jessica was going to be difficult while trying to hold my anus shut. The dawning realization spread through me. To fuck her I had to let him fuck me.

"Let me in, just open and relax and it will soon feel so good." He cajoled.

He pushed a little deeper. His cock opening my tight hole just a bit more.

Jessica kissed me, whispering, "Come on stud, I need your big cock grinding me. Do it, let it happen, just fuck me and let him fuck you."

She started churning her hips under me. The feeling of fucking took hold of me and once again I let pleasure overrule my logical mind.

My resistance as she ground into me melted. I accepted my fate, desiring the pleasure of her pussy over the need to protect my ass.

Fully aware of what was about to happen I began pumping her in time with her thrusts, faster and faster, deeper and deeper, the feelings of ecstasy pounding back through my whole body.

As she groaned and grunted under me, she spread her legs open and I pushed her knees up near her tits to allow my cock even deeper access to her hot pussy.

I pumped harder and faster. Ted held his cock still in my ass as he squatted above me. Each time I pulled out of her I plunged his cock deeper and deeper into my ass. Each time I plunged into her sopping cunt Ted's cock slid out to the edge of my now relaxing brown ring.