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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.
