Golf Sextacular (PM Homerun2611 before posting)

[TiffanyNylons]

DRAMATIS PERSONAE:

William "Bill" Craig:
https://i.pinimg.com/736x/be/90/ca/b...shion-blog.jpg
Sexual personae: Alpha

40-45 years. Bill was widowed 5 years ago, when his wife died in a plane crash along with his 10 year old daughter. Since that time, Bill has dated occasionally, and as a younger middle aged attorney, partner in a small but prestigious local firm, would be thought of as a bit of a catch.

However since he wife’s death he had objectified women and thought of them as mere tokens of pleasure, he was not sure when he would be ready to resume a true relationship. He believes in the work hard play hard lifestyle and enjoys weekend boys trips, late night poker games, or high stakes golf games at the club. He has a solid gang of friends, some married, some not, but they all live by the “what goes on in Vegas, stays in Vegas” mindset to their questionable past times.

They all know enough about each other to do quite the black mail however since all are active indulgents in the activities, it is not an issue. His core group is the big 4, high stakes golf games every weekend, and high stakes poker at least once a month. Together they enjoyed some of the finer things in life and happily sucked the nectar.


Claire Sinclaire:
https://fuskator.com/full/lFQdPgglu...with-Plump-Pussy-Wearing-Leggings-in-Bed.html
Sexual Personae: omega

Claire is 21 and a new school teacher in town. She came from a small, conservative town and family. She was also an omega, the type who does not realize how beautiful she is or can be. She stayed on the edges of social cliques in High School pursuing her own interests and her own style. Her parents did not let her date, something that did not change when she went to Saint Mary's College for Women.

However in college it was where she had spread her wings a bit, actually spread more than her wings in her secret part time job. She began her sexual exploration as a cocktail waitress in a seedy strip club on the outskirts of town. What initially drew her to the venue she wasn’t quite sure, but drew her it did. She couldn’t imagine herself initially as a stripper, those women seemed so confident in their sexuality.

However, management realized it had a diamond in the rough. Reality is she could have been a featured entertainer at the finest of gentlemen’s clubs but central Indiana had no such establishments and that was not her self image anyway. Management coaxed her on stage as fast as they could and she was quickly the most in demand private room dancer they had. As the top girl she was able to make men drool and feed her a bottomless reservoir of 20’s while completely commanding the situation. She had learned some serious skills and made some serious cash which she had largely saved. These savings are what had allowed her to move in to such a high end condo complex on a teacher’s salary.

She didn’t realize she would be the only single person under 35 there. She thought those stripping days were behind her and although she quite frankly missed the ability to so easily manipulate men and shower her with ‘adulation’, in her new role she knew it was incredibly dangerous to even consider indulging in that double life.

Now that she was working at the local elementary school she longed to get a real social life going, but none of the other local school teachers really did much for her, and in suburbia she was surrounded by married men. She had joined the gym to connect, but so far a bunch of overweight sweaty guys trying to hit on her, hadn’t done much for her. It almost felt like she was back at the club the way they ogled her every move, despite the fact she was wearing yoga pants and workout gear instead of a g-string and pasties.

She had started to be interested in an older guy who she had met a few months ago, but so far it was totally platonic. He was clearly successful and didn’t fawn all over her. She wasn’t even positive he was interested. Perhaps he considered her too young or inexperienced. Young maybe, inexperience, it all meant what you were talking about. She lived two condos down from Bill. They had originally seen each other about 6 months ago when they had met in the courtyard. Bill had a golden retriever, Rufus, and was throwing the frisbee around with him when Tiffany was walking into her condo. Rufus was a friendly pup and had come over to say hi, and Bill had apologized for his overture and they had exchanged greetings. Since then they had seen each other a few times at they gym and recently Bill had bought Claire a couple of smoothies they had shared after working out. There seemed to be chemistry, but for some reason Bill had seemed preoccupied and hadn’t pursued and Claire didn’t really know how to initiate. She was used to having the upper hand.

SETTING:

Suburban Kansas City, a suburb of about 8,000 people.

SCENE:

This upcoming weekend is their "Golfsextacular". The “Big Four” had talked about this for a while, but the idea was for each guy to compete to find the hottest stripper/escort, who was ready and willing to be a sexual slave for the weekend and join in completely to the festivities. Each couple would have their own penthouse suite, in a private block of interconnected suites they had booked at the Bellagio for a sordid weekend of high stakes poker, golf and debauchery.

In fact, they already had a $5,000 standing bet on who it was determined had the hottest date, and a second on who ended up with the wildest sex story of the weekend. Bill was a competitor and had every intention on winning! The boys were high rollers and the Bellagio would have their private lear jet at the Kansas City private airport at 9:00 AM to pick them up and take them to Vegas. Let the games begin!

Chapter One​

It is Wednesday evening, and Bill is running on the tread mill at the gym listening to the most recent U2 album and just starting to build a good sweat. Claire entered and smiled at him, she was wearing a purple and black work-out outfit. As she did her stretches, he was aware of the differences from her usual routine. She was stretching in front of his treadmill, usually she did this behind the treadmills where she could maintain some degree of modesty. Not that it really did anything, since the wall mirror gave him a good view of her.

He could also tell that her yoga pants were extra tight tonight, leaving very little to the imagination. They had bumped into each other several times working out and he had become familiar with her routine, and that fairly regularly she would deviate as if she was suddenly confident for about five days. She would pay more attention to her hair, make-up and wear more flattering clothing. He had begun to wonder if she was one of the mythical omegas; a beautiful woman who did not know she was beautiful but with proper guidance she could turn into a sexual animal.

And once a month when she is ovulating: she becomes more confident and outgoing. Less inhibited.

His thoughts are interrupted when his phone rings through his wireless head phones. “Oh hello Amber, are you ready for this weekend … you have got to be kidding!...you can’t do this to me, we are leaving Friday morning and everything is booked, all the guys and their dates are all set as well…. Yeah, yeah, I get it, but what am I supposed to do … Any idea if your friend Mary might be available, she certainly is not you, but we have so many group “activities” planned (Bill has to be very careful, he knows people can likely hear him and virtually no one would approve of the itinerary) … no, no, okay maybe next time and I hope you feel better soon, but I have to go I need to try to come up with an idea fast."

Claire steps onto the treadmill next to bill as he sighs in annoyance and pulls off his head phones. "Sounds like someone is getting stood up this weekend." She says as she starts the treadmill. Her breasts are bouncing as she slowly works up to a light job, usually they are constrained by a sports bra. More evidence of her being an omega? "Professional or personal date?" She says smiling, her heart pounding as she tries to casually flirt and hit on the older Man she is crushing on. "Anything i could help out with?" She quickly adds.

 

[Homerun2611]

Bill, smiles and then outright laughs at her question, "Professional or personal date", ha. What would she think if I said, both, when you have set up a date with former playboy centerfold at $10k per day for her "services" it is definitely a professional arrangement, but the benefits damn well better be personal.

"Actually a bit of both, three very good friends and business associates and I have a plane picking us up Friday morning to go to Vegas along with our dates for a fun filled weekend". Could she help out? Hmmm, I might enjoy that but doubt she would. So how would you feel about competing against three other couples in a littany of sexual games and competitions intended to test our boundaries? "No, I couldn't ask you do do this. You are a lovely girl, but I don't think this weekend's agenda was intended for an elementary school teacher."

Bill starts to put his head phones back in and restart his treadmill, but feels bad bad as she looks a bit disappointed. He turns back around to face Clair and gently puts a hand on her arm, "thank you, I really appreciate it, but I can't imagine this is something you would enjoy, I will need to figure out what my best plan is.'

Bill is still confused by the look on her face, is he missing something, she seems disappointed, but she has no idea!

 

[TiffanyNylons]

My expression is a blend of curiosity and rejection. i am not so naive as you think i am, then i feel your touch on my shoulder. It feels so...hot. My body responds. It would get this way a few days every month; it was horrible when she worked for Platinum Plus as 'Mary Sue'. She had almost given up her virginity several times; but her strict Catholic upbringing had kept her a "good girl". Those were the nights her customers would most often take her up on her offers of the Champagne Room. On those nights she would give head...a lot.

"Are you sure? You have my interest piqued now, perhaps you could buy me a smoothie and we could talk about it if you want to go somewhere more private."

My cheeks flushed with a natural blush from both embarrassment over my out-of-character boldnees...and my body's natural reaction to ovulation. Along with my lips naturally reddening and an over all glow. Not only these physical signs, but my body also radiates phermones....

 

[Homerun2611]

“Piqued interest...you would like to learn more?” Maybe my Omega intuition is right, is there more to this girl than I think. I looked into her eyes as I decided how to respond.

Since my wife died, I have had virtually no girlfriends, or more appropriately friends who are women. At first it was old friends who, while nice, wanted me to dwell with them in mourning and give me pity. No thanks!

I loved my wife, and my daughter, and I was faithful to them throughout our marriage. It damn near killed me when I got the news. But we all grieve in our own way. Mine was to toss myself into work for 6 months and when I came up for air, the spring sprung. I did not want relationships, I wanted release. I fucked in anger and resentment as often as passion. They aren’t mutually exclusive. I fucked a lot. I found my pleasure in a combination of call girls and one night hook ups where I benefited from their self loathing. We were a mutual release with all the emotional ties of eating a good steak or playing a great golf course. Ha, I actually played some dog tracks as well, if I am honest with myself.

Guys often joke that the perfect wife is a princess in the daylight and a whore in bed. Very few find that combination in a single person. Cheers for those that do, I didn’t. My wife had been a princess: classy, smart, beautiful and charismatic. She knew how to handle herself in every situation. But she was nothing spectacular sexually, boring to be honest, but I had loved her. Since her passing, I had many whores, professional and otherwise. I had avoided complications and emotions like the plague, and took solace that either I could care less about their feelings or as that modern philosopher, Charlie Sheen, once joked, “I don’t pay a call girl to sleep with me, I pay her to leave”.

I had met Clair a few months ago, by chance (thanks Brutus), but we had continued to run into each other serveral times and had gotten to know each other a bit and I had actually enjoyed her company. Not fucking her, or trying to convince her to suck my cock, but talking, sharing a laugh, learning a bit about each other. She was young, but there was something so much more there, special, intangible. I found her sexy as hell, but I had never considered adding her pelt to the wall. Conquests had been easy, friends/respect not so much. Did I want to even consider introducing her to my sordid side? I had things I would enjoy teaching her, but deep down I knew I would miss this friendship if I lost it, and that was the likely outcome. I had made sure to keep it platonic, and it was arguably, other than maybe my secretary, the only healthy relationship I had had with a women in 5 years.

But as I looked in her eyes, I touched her cheek, and I saw something. I am not sure what possessed me and before I even realized it, I was saying, “sure let me go get us some smoothies, and I will meet you in the lounge, it should be pretty empty there now and we can talk.”
I went to the café, picked us up two smoothies, then I walked into the lounge. As I walked into the room, I realized we were the only two people there, but where do I start and how much do I tell her? This feels like a very bad idea...

 

[TiffanyNylons]

i blush when Bill breaks the touch barrier and caresses my cheek; i react timidly...femininely. Then he suggests we head to the lounge and he'll buy us smoothies. Never one to turn down a free smoothie from a hot guy, i head towards the lounge and pick out a cozy little booth in the corner.

i find myself eager to learn what he has planned. This was a guilty pleasure of mine when i danced as Mary Sue; listening to the various fantasies of the Men who had me sit on their lap or let me take them to the couches for lap dances. These fantasies ranged from the mild to the wild. What was strange was some of the most mild were from guys who looked creepy; while the wildest and craziest cam from normal looking guys.

Like Bill.

That had her interest piqued as well as aroused. She had found that she enjoyed some of the more intense...and dark fantasies.

i smile brightly, warmly as he walks up with the smooties. i even stand. i take the one offered to me. "Thank you, Bill...so what is this secret of your's?"

 

[Homerun2611]

I see her over in the corner. Good, it is a bit darker over there, and even if someone walks in they shouldn’t be able to hear anything. He laughs to himself, hell even if she runs out screaming I can slip out the back before anyone sees me.

Bill is wearing grey, loose running shorts and a baggy dark blue shirt that matches his eyes. As he walks over to Clair, she stands up and smiles. Her smile is beautiful. As she reaches out for her smoothie, I notice something else. Her nipples appear hard through her top. I don’t think it is cold in hear so something has aroused her. We’ll see if that lasts.

We sit down on the bench of the booth, and I sit next to Clair. I raise my knee and have it bent across my other knee. As I turn to face Clair, my bent leg runs along her thigh. I want to see her reactions, and figure out, how far I can go. I look down at her tits one more time and take a deep breath. Here goes nothing.

“Clair, we haven’t known each other long, and you don’t know me very well. I have really enjoyed getting to meet you and talk to you, and I don’t want that to end. I am going to tell you some things that may shock you, but please if I start to go anywhere that you aren’t comfortable hearing, just speak up and this conversation will be over.”

“This trip that my friends and I have planned is no ordinary boys weekend. It is our first, and we will see if it is our last, trip we are calling the Golfsextacular.” I laugh nervously, “I know that sounds a bit corny, but I believe it will live up to its name.”

“We are being picked up by private jet that one of the guys arranged with the hotel and we have a set of interconnect suites set up at the Bellagio. There is a reason for that, there is likely to be significant drinking and partying, some sexual exhibitionism, and there may even be some interaction across the couples. Some of the guys dates are actually high end call girls, but all of the girls know what this weekend is about. No one will be forced to do anything they don't want to do, but you can expect this group to be pretty much up for anything!”

Despite himself and his concern as to what Clair must be thinking, as he begins his description, he can feel his cock tingling and beginning to get hard. He looks down, at least nothing is too obvious yet. He looks at her closely and again touches her shoulder, he wants her to look at him, her nipples are even harder, but that doesn’t mean much. He pauses to check her reaction…

 

[TiffanyNylons]

Your leg...your knee brushes against me...my leg in an accidental, yet intimate way. Color fills my cheeks, but not a blush of shame or embarrassment but arousal. i can tell you are staring at my tits, i find myself pushing my breasts out subconsciously like when i was dancing.

i can tell he is awkward, which is out of character for him. Then he begins explaining what he has in mind. He finishes and then places a pensive hand on my shoulder in a gesture i find...sweet.

i slide closer to him.

"i have a few things to explain too..." i am no longer that afraid telling him my history. "...i had a wild side in college. i was a stripper at a club in central Indiana for about three years. Now i was not a slut, and this may sound absolutely crazy...but i am actually a virgin. Yes i gave lap dances and went to the Champagne Room...a lot. But all i gave guys were blow jobs. i came from a good, conservative family...and i am actually a good, conservative girl." i take a deep breath. "But that is on the streets...and how does the saying go? A whore in the sheets? i want to become very sexually adventurous but with a good guy." i blush again, this time in embarrassment. "Now i have an extra time of the month...i have the normal crying, hormonal time...but i also have this insane drive for several days to just..." i look at you, then away as i finish this sentence. "...fuck."

"And i can see myself starting to...start this other time of the month."

 

[Homerun2611]

She definitely isn’t running away. I smile at her response. I am a bit shocked, but I am even more intrigued. “i was a stripper at a club in central Indiana for about three years. Now i was not a slut, and this may sound absolutely crazy...but i am actually a virgin. Yes i gave lap dances and went to the Champagne Room...a lot. But all i gave guys were blow jobs.”

If I wasn’t before, I am hard now. I picture her beautiful mouth and tongue on my cock and I want it. We haven’t even kissed and I want to feel the warmth of her mouth slathering my dick. I hope she swallows!

A heterosexual, virgin, stripper, I almost chuckle at that, that is more rare than a unicorn!

I think she is also telling me she is in heat …my cock gets even harder.

Woah, I don’t think she still completely gets it. “Clair, okay, perhaps you aren’t quite the innocent I thought… By the way, I like that” I smile at her, and turn both her shoulders to face me directly. “but giving the occasional blow job in the champagne room behind a curtain, is very different than doing that in a room where everyone can see you. Can you be vulnerable like that? We already have two bets on the line for this weekend, the first $5,000 is for whomever brings the sexiest date. The second is for whoever puts on the hottest sexual show. While you definitely have a good chance of helping me with the first, I fully intend to win both. Are you willing to put on a show? This entire weekend is about tittilation and indulgence … on the plane, in the hotel, in the casino, on the golf course. Can you be all in?”

I am still holding her shoulders, and looking into her eyes, I can’t help myself and I lean forward to kiss her, and as I do, my hard cocks presses into her leg …

 

[TiffanyNylons]

You kiss me before i can say "Yes"...i close my eyes as you do. i can feel your cock rubbing against my leg.

When you release me, i look around...seeing only the smoothie bar employee...i slide from my seat and onto my knees under the table. i look up at you from my knees, my hands sliding up your thighs towards the waistband of your shorts. "Is this a good start?" i ask, as i start to pull your waistband down, revealing your cock. My soft, warm hands slide around your shaft, softly stroking you.

i lean forward, pressing the tip to my lips for a kiss. My tongue slides out, sliding around your head as i lick the precum from it. Yes you have been working out, and i can taste the sweat...but i have tasted worse in the Champagne Room. i had learned the hard way that just because a Man looks clean does not mean he will be clean in his pants.

i slide one hand under your balls, cupping them. Caressing and teasing them with my fingers as i stroke you. i press my face forward and take your cock into my mouth, sliding down and impaling my face on your cock. My tongue dancing along the bottom of your shaft as i start to suckle.

It has been awhile since i have sucked a dick; i did not realize how much i missed it. There is something so feminine about being on my knees pleasuring your Manhood.

 

[Homerun2611]

Our kiss was relatively quick, but electric, I was pretty sure I had interrupted something you were about to say with my impulsive movement. I briefly had slipped my tongue past your slightly parted lips, and loved how your lips met mine and your mouth and tongue welcomed me in. A first kiss tells me a lot about how a women’s body will respond to mine, and my instant conclusion was this woman could be an incredible lover.

However, as soon as it started, our kiss was quickly over. I loved your wicked little smile and spark in your eyes, but what was even more impressive was the almost feline quality of your movement, as you slid down between my legs. I feel your hands on my inner thighs as your hands reached for the wasteline of my shorts, “is this a good start? you ask. My body is instantly aflame with anticipation, “Couldn’t be better!”, I say half moaning as I await your touch.

I feel your warm hands on my shaft and am sure I am oozing precum to show my body’s appreciation. I part my legs slightly and slide towards you a nudge to make your access as easy as possible. As I do this, I realize, oh god I worked out before. I like my boys to make the best impression they can. I don’t want to break your assault now by apologizing for my musk. As we move forward, she will see, as she goes down, my cock, balls and ass will be as clean and inviting as I can make them.

“Oh god, oh yes” I groan as you gently kiss the tip of my head. I love when a woman fingers and tongues the meatus. I squirm and moan a bit more. I feel you lick the precum and I can tell you enjoy it. A man can tell when a woman feels like she is doing you a favor or if she enjoys it, and it makes all the difference. “ Ooohhh, god” I moan as you cup my balls and stroke me. “Be careful there young lady, a woman who can play and tease my balls like that, just may steal my heart”, I am only half kidding, quality ball play raises the intensity and enjoyment of a blow job exponentially.

Finally, I feel your lips close around my cock and go down. When hard I am 7 to 8 inches, with medium thickness. I am circumcised and the tip of my dick is incredibly sensitive and responsive. As aroused as I was, I was sure I was pushing my limits. I could literally feel my heart beat in my cock. You took it like a champ, continuing your tongue play all the way down until I felt your lips at the base of my cock and my head in your throat. No gagging, no wincing, just incredible technique. “God, you are an unbelievable cock sucker!” I can make no greater sexual complement. I love oral, and this was as good as it gets. Clair was not giving me a blow job, she was making love to my dick with her mouth and hands, and my cock was a most appreciative and responsive lover.

“Oh baby, this feels incredible...you are incredible” she was putting on a show and I was impressed, she was a performing artist and I loved being her canvass

 

[TiffanyNylons]

i smile, you seem to be enjoying my sucking. i find that i feel better about myself when pleasuring a Man and that i actually miss stripping. i miss being 'Mary Sue', erotic nerd girl. i pull off your cock and look up at you. "Swallow or wear it?" i ask you. Some of my Champagne Room customers wanted me to swallow, others enjoyed cumming on me and making me traipse through the club with their mark on me.

The question asked, i go back to sucking. Slowly i push your cock back into my mouth...taking it deeper and deeper into my throat. Swallowing you. i gag a little, massaging your shaft with my spasms. As your cock disappears into my mouth, my tongue snakes out and licks your balls.

 

[Homerun2611]

"Swallow or wear it?" For me, a woman never looks sexier than when she is down between my knees impaled on my cock. I have panted many women, but what I most enjoy is a woman who completely milks my cock, sucking out every bit of my nectar. I tend to shoot a powerful and very full load and I love it when a women, happily, appreciatively takes my load without missing a drop and swallows. The perfect end to a perfect moment.

I utter a singular esponse "SWALLOW!"

 

[TiffanyNylons]

i hear the command and obey; furiously sucking your cock. Making love to you with my mouth. My hands stroking up and down on your cock, eager for my reward. My eyes glance up at you time to time over the rims of my glasses. i can feel you are close...

Then you erupt inside my mouth. Shooting rope after rope of cum down my throat and filling my mouth. i swallow every drop and then obediently begin lapping at it. Cleaning it before tucking it back inside your shorts and then sliding back into my seat next to you.

"So what time Friday do we leave?" i ask with the confidence that comes once a month...

 

[Homerun2611]

"oh god....ooohhh YES.....that feels so good" I want her to hear and not just feel how good she is making me feel. I even buck my hips slightly but know she is confined by the table. She picks up the pace, deep, long, excellent, faster, I feel it erupt from by balls and explode into you, over and over. You take every bit, and swallow with enthusiasm. I can't take my eyes off you. After I cum, you stay on my dick, sucking and cleaning every last drop of my cum.

You come up and sit down next to me grinning, GOOD GIRL. "So what time Friday do we leave?"

I grin at you, "well you have certainly been full of surprises. Are you really sure you want to do this with an audience ... and more?" I get serious for a moment, "Clair, kidding aside this was terrific, but there are a couple of things. One, you are a virgin. Even I am not a big enough cad, to think a girl losing her virginity should be a spectator sport, however this weekend will involve fucking ... lots of it. If you really want to go, and are comfortable with me being the first, let me give you the private experience you deserve. Tomorrow night would be all about you, and my attempt to absolutely satiate you. I am actually a pretty good chef, so let me know what you would like me to make and give me the opportunity to make that a memorable, and private experience. So from now until then you have the chance to reconsider, and I wouldn't blame you one bit. This, right now was terrific, the Sextacular will be a whole different ball game. Anyway, I will be ready at 7:00 PM tomorrow at my place. If you show up, I will know you have thought this through, and from that point on, I won't ask you again. I will have given fair warning. "

"Second, here is the fun part. Your job this weekend, all the ladies jobs, is to be as creatively enticing as possible. This is a sexual competition. We will have fun and we will be on the plane, in fine restaurants, dancing and clubbing, in casinos, at the pool, on the golf course, and of course in our suites. My hope is that my dick is motivated to be hard throughout. Part of your role is constant visual encouragement. You may have some applicable wardrobe from your prior career" I grin and rub your thigh. But I expect you to probably need to supplement your ward robe. Be true to your personality, but be creative and test yourself. When I get home I will drop off $5,000, just let me know if you need more. Dresses, gowns, shoes, lingerie, costumes, swimsuits, sport wear, toys whatever you need or want. Accessibility for my fingers and other are always appreciated. " I grin again and slide my fingers up your yoga pants.

I lean over to you and now press my hand firmly against your pussy, I whisper into your ear, "I look forward to pleasuring your cunt."

With my hand still there kneading and applying slightly more pressure, I kiss you long and slow, I feel your mouth respond and I can taste a bit of my cum in your mouth.

We finish the kiss and I then get up and look down at you. "I am headed off to shower, I will drop the money off before I leave in the morning, and I guess I will see if you are there tomorrow night...oh, and the limo picks us up at 9:00 AM sharp on Friday, if you are going I will knock on your door at 8:55 and help you with your bags". I start to walk away and turn around, "I love surprises!" I grin, turn around and begin to walk to the showers. leaving you to think ...but then turn around again, "and what should I get for dinner?"

 

[TiffanyNylons]

i notice that you are less hesitant with touching me; instead you are more possessive. Your hand on my thigh. Your words, telling me that if i agree i will be a sexual object, but at the same time you care enough to worry about my well-being. The thought of you being my first, a dominant older Man who is willing to take what he wants when he can turns me on so much. i can feel my pussy opening, getting wet...i am pretty sure when you cup my cunt you can feel just how hot it is.

Another sign that i am in heat.

i watch you leave, then turn around and ask me what i want for dinner. "i like Italian."

i stand up to leave, as i pass the smoothie clerk he is smiling at me...grinning knowingly as he watches me intently. i find out why when i get to my condo; there is a drop of your cum on my chin and my yoga pants have a wet spot where your hand was. i am at once ashamed and very turned on...i hurry to my bed and start to Jill-off furiously thinking about losing my virginity to you tomorrow night...

 

[TiffanyNylons]

Chapter Two​

My heart was pounding as i got ready for my date with the handsome older Man in my condo. i had gone to my principal and told her that i had something come up and i had to leave town Friday morning. She expressed concern and hope that everything was okay, i smiled and assured her that it was. So she scheduled a substitute teacher.

After school i hurried home and spent some time sorting through my old stripper outfits. My stage name was 'Mary Sue' because i am a huge nerd and geek; i love science fiction. So i would dance as Princess Leia (i had costumes for white gown Leia and slave Leia) or a blue uniform from Star Trek--the original series from the '60s where the women wore short dresses, tights and go-go boots.

Then i pulled out my secret box.

One thing that i have always known about myself is that i am a natural submissive. Perhaps this comes from growing up where i did with strict parents who were happy in traditional gender roles. Which is probably why i like older Men; they seem more in control of themselves and those around them. Which leads me to my secret box. i love self-bondage. On the weekends or after a stressful day at work i will slip into my favorite BDSM teddy or chemise and lockable wrist & ankle cuffs. i then pull the blocks of ice out of the freezer that have keys to the cuff's locks and lock myself into a kennel for an hour or two. Sometimes i put the kennel in my living room and leave the door unlocked. People in the condo do not just go around trying doors to see if they are open so i pretty sure that no one will barge in and catch me. But the thought that they might...

But that is not what tonight is about.

i have a new bondage bra and skirt set that i have been dying to wear. So after a shower i slip that on, minus the g-string that came with it. i slip on a pair of pink thigh highs and a sporty black dress. i like the color on my legs, it pops in a youthful fun way that i hope Bill will enjoy.

Once my hair and make-up are done; i look at the time. It is 6:45, i wonder if Bill minds guests showing up early?

But before i go, there is one last decision to make. It is one i have been grappling with; the bra set is definitely BDSM but not necessarily in the most obvious sense. i was considering wearing my collar just so he knows what kind of girl he is getting when he opens the door. Looking in the mirror i smile as i make my decision.

A few minutes later there is a knock at your door; when you open i am standing there. Collar on my neck and, save my stockings, barefoot...

 

[Homerun2611]

Since I left her at the gym, all of my thoughts and activities had been centered on Clair. I had made a back up plan, with a local escort if she didn’t show up tonight but I preyed that wouldn’t happen. The excitement of our trip had somewhat surprisingly taken a back seat to the opportunity to deflower this beautiful young girl.

I had had two virginal experiences in my past. The first was at my junior prom, where being a virgin as well, it had all the specialness of an x-rated keysone cops. Given my prior experience had been masturbating to my Dad’s Playboys, and hers had been less, we had taken a few shots of liquid courage and embarked on what proved to be a dry, somewhat mutually painful, and most certainly unremarkable experience. We broke up a few days later, as much out of mutual embarrassment as anything.

The second had been during my sophomore year in college during a sorority mixer. My date, a knockout red head, Bridgette was a great dancer. We were both pretty drunk. It was very dark in the basement party room of the fraternity house. She was the type of girl who loved to grind while dancing, she would continually turn around while dancing, bend over and grab her ankles, and then push and grind herself into your increasingly responsive cock. The last time she did that, she then turned, and whispered into my ear, “Are you ready to drive this race Car around the track?” Yep, I sure was. We had nearly run up to my room making out the entire time. I was as horny as any college kid could be. We ripped off each other’s clothes and attacked each other. As I got on top of her, she screamed, and I mean screamed, “FUCK ME!!” And I did. She was as wet as I expected, and I was a pile driver on a mission. When I encountered some resistance, I drove right through it. I had never dreamed this was my sports car’s first race. Despite the blood, to her credit, she never let on and fucked like a champ to multiple orgasms. Damndest girl I ever met, a true Alpha. We hooked up several more times in college, each encounter slightly kinkier than the past. I ran into her in NY a few years ago and found out she was noe the VP of marketing at a Manhattan cosmetics firm. I smiled when I heard that as AI could only imagine what her national sales meetings must be like.

I had vowed if I ever had another chance, I would make it special for her...and for me. However as the years passed, I had given up on that thought.

I had been up since early this morning. First, I had left the $5,000 in cash in an envelope in Clair’s mailbox. I was looking forward to her unveiling her purchases over the weekend. I had gone to work, but left at noon to prepare for this evening. She had requested Italian, and I would make home made linguini and clam sauce for dinner, with a ceasar salad and homemade garlic bread. Clair would be dessert.

I went to the market and got fresh clams, anchovies, and 2 ounces of bulaga caviar for a special appetizer. I went to the dry cleaners and picked up clothes for tonight and this weekend. When I got home, I put fresh, red silk sheets on the bed, and the little silk pillow I would use to facilitate things later. I also laid red silk sashes om th night stand beside my bed. I set out about 100 candles, and then went about preparing dinner.

By 6:30 I was set and took a shower. I would be casual tonight and I wore tan linen slacks and an untucked button down chambray sport shirt. Brown Italian loafers, no socks, a touch of cologne, and I was ready. All through the day though, even when I picked up a present for Clair to commemorate tonight, I had been concerned, “Would she ctually come tonight, how would I feel if she didn’t?” Those types of thoughts just weren’t me, or hadn’t been in years. Could I really care about this girl?

The Santa Margheretti Pinot Grigio was chilling in the fridge, the scented candles were lit in the bedroom, the caviar was on the cocktail table, and I was just opening the bottle of Cristal when POP, I heard the door knock.

I opened the door, and there was Clair, dazzling, with a wicked smile on her face, and sparkling eyes. Then I saw it, the COLLAR. I smiled and leaned in and kissed her, deeply, passionately. “Welcome my pet...”

 

[TiffanyNylons]

i smile when i see your eyes scan my collar, especially the way your eyes light up when you notice it. Then i am kissed with reckless passion, pulled into your strong embrace. “Welcome my pet..." i feel a tingle between my legs as you call me "pet".

"Yes, Master." i say softly and quietly enter your home.

i can smell dinner cooking, it smells good...but something is off.

As you finish cooking, i sit on your kitchen counter and chat with you. Explaining where i grew-up, how i grew-up. We chat about my experiences stripping and the various costumes. i tell you about the only time i thought about giving up my virginity to my best customer; an airman from a nearby Air Force Base who had recently gone through a divorce. i had even gone out with him a couple of times, always ending the date with head. However, he got deployed before i could give myself to him.

The whole time you are exploring my body. Kissing me randomly. i admit to having fantasies of Clothed Male nude female (CMNF); which leads me to removing my dress. As a glass of wine turns into another then another, my lips are loosened and i spill so many details of myself. i tell you about the self-bondage; in the back of my mind wondering if you will start trying my door when you walk by it.

Finally dinner is done, and i take my place at the table near you. i take the first bite...clams...anchovies...i try to swallow each bite. The sauce is okay; but i am a Missouri farm girl. i'm used to beef, pork and chicken. i like some seafood...like the stuff that comes from Red Lobster...but this more cultured food is difficult for me to swallow. But i try to make a good show; i do not want to insult my host.

My Master.

 

[Homerun2611]

As I cook dinner I learn more and more about you. Surprised, would be an understatement. I am incredibly aroused, but also find myself increasingly possessive. Part of me visualizes seeing you perform, even watching you give you customers head, but looking at your collar, I want that virgin cunt all to myself, forever. Did, I just say that? I also, want to be the first man to christen that virgin ass.

When you tell me your fantasy of CMNF and slide out of your dress, I get yet another surprise. Your bondage bra and skirt, lights even greater passion and accelerates our relationship to the next level of intensity. Earlier in the day while thinking through options, I had contemplated the most stimulating way to take your virginity. Now seeing you in that bra and skirt, I had no doubt, my red silk sashes would come in handy.

My cock is so hard it almost hurts, but it is a good hurt. I can barely keep my hands and lips off you. We kiss passionately, deeply and often. As you sit on the counter, my hands roam freely. Initially, I run my hands along your toreso and arms, we kiss, and I hear you softly moan and coo. Your legs open a touch. I massage your breasts, and lightly tickle you down your stomach to the top of your slit, still keeping myself only on the outside of your lips. You moan and utter something, I can’t quite make out. As my hand slide toward your pussy, your legs separate more. “Not yet” I whisper.

I go back up and truly enjoy your beautiful breasts. I stop kissing you briefly and lightly lick my right index and middle finger. With my wet fingers I circle each of your areolas and massage your nipples, you whimper. I bend down and breath warm air and then blow cool air on each nipple. I lick and suck lightly on each breasts, then I roll your nipples in my teeth.

I come back up and kiss you again, while first rolling then lightly pinching your nipples. You gasp, and move to the very edge of the countertop, you spread your legs as wide as you can and whimper. I smell your arousal as your pussy lips open up, and adrenaline courses through my veins. RESTRAINT, PATIENCE, I yell at myself in my internal voice. I kiss you harder and slide my hand yo your pussy, I trace up and down your inner lips, once, twice, three times. You whimper louder. On the last track I stop at the top and feel your clit. It is engorged and you literally yelp as I touch it. I massage it for no more than 3-5 seconds and feel your body wiggle, as your lips stay plastered to mine and your tongue wildly searches in my mouth. This girl is an animal I can’t wait to tame. Lastly, I take my two middle fingers and slide them gently but steadily into your cunt. Your pussy is dripping. Your mouth breaks free, and I think I hear you say, “please fuck me Master”. But you are breathing so hard it is hard to tell. That is what I hope you said at least. I smile, and with my two fingers now deeply in your cunt, I firmly grab your pussy. “Not yet my PET , tonight is all about you, pleasuring you relentlessly, until your pussy is mine. Until, you understand that no man will ever be able to pleasure your cunt like I can, and all you can think about is having me pleasure you again”.

“Now, I need your strength up, dinner is served”. As we walk to the table you tell me about the self bondage, and I am even more aroused. That is an opportunity to contemplate for another time, but an opportunity indeed. My cock is so hard now, I am not sure I can even sit down.

Somehow I manage. I watch you as you’re trying to eat. Clearly something is wrong, but you are too polite or respectful to say. I need you to eat and.while not exactly gourmet, I have an idea, one that will help us both feel better. I am in pain as I sit, I am so sexually charged. I get up from the table, and go into the kitchen. I unwrap a Stouffers spaghetti dinner from the freezer and put it in in the microwave and set for four minutes.

I grab the package I purchased for you earlier in the day. It is a 5x5x1 inch box wrapped in red satin paper and a white boy. With it I have a single white, virginal rose. As your dinner cooks, I walk over beside you, and I squat down and look you in the eyes, and clasp your hand. “Clair, please accept this present to commemorate the night you gave me your virginity. It is sweet and a gift like no other. For as long as you own this, I hope when you wear it, you will remember this night and the pleasure you experienced”.

I set the present down next to you. I stand up and spread my legs solidly apart. As you are still facing me your eyes are level with my belt buckle. You lick your lips. “Now my pet, you have made my cock so hard, that I need you to clean it.” I can feel the precum wanting to explode from my engorged penis. “We have one minute, and I need you to make sure my cock is clean and ready for you when your dinner is complete” I know there is only 60 seconds until the timer will ring, and I don’t want to cum, but I need to feel your mouth on my cock for at least a few seconds before I burst. I unzip my pants, and my cock springs out of my trousers. “Now, my Pet...”

 

[TiffanyNylons]

My pussy is pulsing with need for you; to have you inside me. i also need to have you...finish inside me. i have not been able to think about anything but you, specifically having you cumming inside me. Every time you have brought me to the edge, i have been able to think of nothing but having you fill me with your seed.

However, i notice you putting the TV dinner in the microwave and i am grateful that you are not making a big deal about this. Then you bring the box over and hand it to me; i resist the urge to tear into it...but i resist. You seem to want me to show restraint. Then your cock is in my face, so i lean over and take it in my mouth. i do not wait, i do not take my time to worship your cock. i take it in, as far as i can. i do not worry about my gag reflex. i inhale your cock. My tongue dancing along the bottom of your shaft, sneaking out to lick your balls.

My gag reflex quivering and spasming along your cock, milking it.

Then the timer goes off...

You pull your cock out my mouth. i can tell it took a lot for you to do so, you go and get my spaghetti TV dinner from the microwave and bring it to me while i smell the rose you got me. We continue eating; making light chat. It seems we both need to calm our discussion if we want to make it through dinner. The gift stays within my sight; i am curious about what it is...

Finally dinner is done and i clear the table for you. i return to the table and hold up the small box. "May i, Master?" i ask...

 

[Homerun2611]

I am pleased that you are finished. I want you strong, but I cannot wait to begin. "May i, Master?"

"Yes, you may" I see you gingerly open the package, and I believe you are delighted. Although, In all honesty I had not meant it quite to the extent I believe Clair perceives it, I had intended it to signify the bond we would create tonight, and how I would ever be the first. But her showing up as she did, and the glee she demonstrates as she puts in on, makes me think of it as so much more, it is beautiful on her, and I want it to mean she is mine, I own her. I can't wait to make love to this woman to become her Master.

I had gone in the jewelry store looking for the right gift and the minute I saw the diamond choker, I knew that was for Clair. Tonight I planned to own her, it was time to begin. I went into my bedroom and came back with on of the silk sashes I had put by my bedstand.

"Do you like it? Do you trust me?" I said looking into her eyes.

I walked behind her and I put the sash around her head covering her eyes. I guided her up, and led her into the bedroom. Once there, I removed her remaining clothing. I laid her down on the bed, with her hips slightly tilted up by the silk pillow I had previously placed on the bed. As she lay on the sheets, blind folded and open to me, she looked beautiful. I had never wanted anyone more.

I laid down next to her and slowly began running my hand across her body. Playing with her breasts, lightly tickling her stomach, and pressing into the folds of her pussy. "You are extraordinary, relax and enjoy this".

As I began to play with Clair, her body began to respond, her nipples hardened and she opened her legs to provide full access to her sex. "I believe you are ready, tonight is about you, but I am in control. You are beautiful and I will do everything I can to make this the most erotic experience of your life. Are you ready to begin?"

 

[TiffanyNylons]

The collar is amazing, perhaps the most beautiful piece of jewelry i have ever seen. i take off my leather collar and replace it with the diamond studded one. As i make the change, you disappear into your bedroom and then return with the sash covering my eyes.

i am led into the room, my heart is pounding in anticipation. And a little fear; i am putting a lot of trust into you. But something about you puts me at ease. i have never felt so beautiful; so special. As you guide me onto my back on your bed, i put my hands above my head in a natural pose of submission. i do not know if you have anymore of these sashes; if you do i want to make tying me up easy.

Then i feel your hands on me, caressing and exploring. Teasing my nipples. As your touch heads lower, my legs spread open for you. My virgin pussy, already explored by your fingers and finding my hymen resisting them, open and moist for you. "i am yours tonight, Master...please enjoy the gift of my body."

Something strikes me, did i tell you about the pills i am not taking. "i...i'm not on any kind of birth control."

 

[Homerun2611]

"i am yours tonight, Master...please enjoy the gift of my body."

Oh I will, I will. "Clair I will take care of you, you are mine and nothing will hurt you. If ever you want to stop, you just say BLUE, and I will stop and end this evening" I then bend over and kiss your lips, "but I am confident you won't want to!" You have raised your hands in submission, and I am beyond aroused. I promise myself to first focus on you, but the heat in my loins, and the heart beat pounding I feel in my cock is almost too much to bear. I love seeing your hands over you head, and I get up off the bed and grab another sash. I have four sets of hooks attached to both my headboard and footboard of my king size poster bed. I attach the tie one sash to your right wrist and the other to your left and tie each hand/arm separately to the bed so they are extended over your head, but not so tight as to be uncomfortable. I want you to be able to writh and squirm and truly enjoy this night.

Your body looks spectacular with your hands tied over your head, your breasts tight, your legs spread and inviting. i get on all fours on top of you. First, I kiss your mouth and you raise your head hungarily to meet me with your tongue. I run my hands down your extended arms as I kiss you, you can feel my cock laying on your stomach.

I want and need you to take a taste, and I move my body up and place my cock at your lips. As you did at the table you do not hesitate. You open your mouth, extend your tongue, and jerk your head up to the extent your constraints will allow to get as much of my cock in your mouth as possible, you aggressively twirl your tongue and lick any precum that remains. "Oh Clair, I love how you worship my cock". I try to pull back and you fight against my withdrawl. "Pet, we are just beginning".

I begin to kiss down your body, as I move, you can feel my erect penis sliding against your breasts, stomach and working its way toward your pussy. I kiss your neck, your shoulders and on down until I reach your breasts. I cup each breast in one hand and begin kissing and licking your nipples. I lick, suck, bite, suck and lick again. I find your breasts perfect and I want you to see how much I want them. As I kiss, lick and suck on you breasts, I hear you say, "please just let me have your cock for one minute, I have to suck you or fuck you, I can't wait".

"Patience, Clair, you will have everything over and over. If I have my way, you will barely be able to walk in the morning, you will have been so thoroughly and completely fucked!". You smile and I continue my way down to my real target. I kiss down your stomach, my tongue plays in your belly button and then I slide down between your legs. You are responsive and raise your legs and spread them as wide as you can. I smile and lean in to smell your arousal. I place my arms under you and lift you up on my shoulders so I can feast on your femininity.

The heat that rises from your vagina is palpable. My cock twitches instinctively to your heat, and I want to feed you my seed. Just not yet, and my tongue enters your pussy. I bask in the flavor and aroma of your cunt. While I always enjoy providing oral pleasure, this is special. I want to make this woman quack. I work my tongue up and down the inner folds. I flick your clit with my tongue and massage it. I see your wetness leak out to your outer folds. I lap that up and again lick up and down the lips of your pussy. I insert my tongue and fuck you with it, while my thumbs massage your lips and clit. I feel your hips buck up and against me as I continue to tongue fuck your cunt.

I give you a glimpse of what is to come later. I lick down to your perineum, pull back and gaze at your glistening open cunt and asshole. I let my tongue wonder down and tongue you starfish to see your reaction. You say something, in a moan that I can't quite understand and then hear you moan, "YES", you push your ass into my tongue and I respond by probing for a bit. "Good, she likes anal play", I say to myself. "I will be back". I want every bit of you, but I want you to come and you look like you desperately need to come. "Please, please" you groan. I make a mantal note that I will get to your ass shortly, but this first orgasm will be entirely focused on your sweet, sweet cunt.

I go back and focus on licking and massaging your clit, and then sliding down and tongue fucking you while I continue to stimulate your clit with my thumb. I pick up the intensity, you wiggle you moan, you bite your upper arm. I am relentless and attack your cunt over and over. You buck into my face and tongue violently. All of a sudden, your entire body spasms, and I hear you groan/scream, "Oh Master, I am coming!"

One, I think to myself and smile. The room is dark other than the 100 candles. I move up your body and remove your blindfold. We have only begun, my sweet ...

 

[TiffanyNylons]

No lover's prisoner has ever loved and cursed her bondage as much as i do right now. i squirm and writhe as i come down from the first orgasm someone has ever given me. My nylon clad legs and feet rub you as you explore my body and do things to me.

i never thought that someone would rim me; when i was stripping the random guy would focus on my ass. Sometimes they would ask if they could rim her in the Champagne Room. She never took them up on their offers; she never saw herself as liking that. But it feels so good when your tongue laps at my rosebud. i make the mental note to repay the favor...

My pussy is open, heat wafting off my fertile cunt. i have a primal need to have you inside me. To have your seed inside me. "Please, Master...fuck me..." i whimper. "Please, Bill..." i say softly, pathetically.

 

[Homerun2611]

I hear your whimper..."Please, Master...fuck me...", "Please Bill...", but it is not pathetic, it is beautiful to hear her. It tells me absolutely how badly she wants my cock, how her womb craves my seed. I had initially to give her a few more orgasms orally and digitally first, but I cannot deny her any longer, she will have her multiple orgams, but now is the time to taker her virginity.

Part of my thinking had been to make her vagina as aroused and relaxed as possible, but it would be hard to be any more aroused, her cunt is so hot and swollen it almost burns to the touch.

I go to the top of the bed and remove her restraints, I want her to be able to give herself completely.

As I do so, I bend down and kiss her, she wraps her arms around me and pulls her self up to attack my mouth, "Oh Master, is it time?"

Her lips are nectar and her kiss reverberates through my body, but I pull her arms away and let her fall back on the bed. "Yes, it is time, I want your womanhood"

I go to the end of the bed, my cock is rigid hard, as hard as it can possibly be. I spread your knees, and I slowly bend into you and feel my cock at the entrance to your wet and yearning vagina...