2 comments/  61125 views/  21 favorites

A Bet's a Bet

By: lollipop77



(Note: this is just fiction, a pure fantasy given to me by a female friend. So I wrote it for her. There is some guy on guy stuff at the end, if you're not into that, that's ok, don't read on. If that's ok, then I hope you enjoy it. That being said, story on) 



Marsha's body awoke to the familiar feeling of her lover's hand slowly running his fingertips over her. Not sure if she was dreaming or the feeling was real, she kept her eyes closed, if it was a dream she was going to enjoy every last minute of it. His fingertips gliding slowly over her stomach, up to her breasts, around each nipple, teasing her like he knows she likes. He ran his hand down, slowly approaching her now stiff clit, her back arches trying to get him to rub her clit, his hand stopping, then sliding down the inside of her thigh. A gentle sigh escapes her lips as his hand starts to back up, again arching her back daring him to run his fingers over her, his fingers barely grazing over her wet pussy lips, her nipples now hard with excitement as his hand moves towards them. Needing to know if this was real or a very vivid dream, she opens her eyes to see her lover Jim, watching every move of her body as he continued to tease her into a sexual frenzy.

"Morning baby" he says as her eyes finally focus on him. 

"Mmmm, morning honey, I love your wake up calls" she says with a giggle. His lips press against hers in more passionate than usual good morning kiss, her tongue sliding deep into his mouth as she pulls him closer.

Jim's right hand continuing to tease her now fully excited body, Marsha's tongue now working faster and deeper in rhythm to his teasing hand. His hand slowly approaching her now dripping pussy, her mind wishing he would slide those fingers deep into her. Again, he stops, "awwww" slips from her mouth, knowing he's in full tease mode now. Without hesitation or warning, his hand slides over her clit and his middle finger is buried deep into her waiting pussy. Her mouth moves off of his, all her breath comes out at once, head back, back arches to draw him deeper. Jim takes this time to take her right nipple into his mouth, sliding a second finger deep into her; he can sense she is right on the edge of Cumming. Taking as much of breast into her mouth and flicking her nipple back and forth, he works his two fingers up and down, rubbing her G-spot, knowing she will cum, and cum hard. 

"Honey, honey....." was all she could get out of her lips as she came, squirting all over his hand. Marsha pulls his face to hers and kisses him, sucking his tongue deep into her mouth. Knowing once she starts squirting it's easy to keep it going; Jim continues to work his fingers inside her. 

"I'm going to squirt again" Marsha says as she begins to fill his hand again. "Now it's my turn to make you squirt" she says, pushing him back down onto the bed, slowly she starts sliding her soaked pussy down onto his thick hard cock. As wet as she is, she knows she has to go slow to take it all in. He reaches up and starts playing with her breasts, leans forward to suck one nipple then the other. He can feel her pussy dripping down his cock, over his balls and onto the sheets. She starts to raise and lower herself on and off his cock, slowly increasing her rhythm, now riding him all she can. She sits up straight, arches her back slightly, reaches behind her and begins rubbing his balls.

Knowing how much this drives Jim crazy, she wants him to cum and cum hard. Sensing he is getting close, she takes her right hand, rubs her clit back and forth, and slowly slides her finger into her pussy along with his cock. Removing it from there, still dripping she takes it and slides into Jim's ass, sending him over the edge "Yes yes yes...." As he fills her pussy, Cumming deep inside her. She lays her body down on top of his, kissing and cuddling in the afterglow of another good morning. 

"What brought this on?" Marsha asks.

"Well, you know I love to make love to you in the morning". 

"Yeah, but this was different somehow" she added. 

"Well maybe I want to start this day off right, and if you want to be really naughty later, we can finish it off even better" Jim says with an evil grin.

"We haven't been naughty in awhile, but I seriously doubt you can finish it off better than it started" 

"Is that a bet baby?" Marsha thinks for a second, knowing how naughty Jim can get, and wondering if it could get better.

"Yes, yes it is, if you can make today end better than it started, I will give you any fantasy you want, BUT, when it doesn't, I get any one of mine I want"

"Ok, it's a bet, but you better pay up when you lose". Marsha's eyes got wide, her mind now thinking, can it get better, and what will he want IF he wins, what will I want when I win, slight smile and giggle escaped her as she thought. 

"What was that smile for baby?"

"Just thinking ahead to collecting on my win" said Marsha.

"Dream on baby, I will be thinking long and hard of what I want for my victory". Little did she know that Jim had been planning something for the past couple weeks. A couple of text messages later and the plan was all set for tonight. "Ok, I have my plans set for tonight, hope you're not going to back out of our bet" 

"Never, I can't wait to collect on my winnings, and I know just what I want" 

"Do you now?" Jim asked. "Yes I do" Marsha says. 

"Can I ask what would be in store for me IF you should win?"

"Only if you tell me what you want if you should win". 

Jim didn't have an idea yet, "I don't have my mind set on anything just yet, can I still know what you want, but won't win tonight"

"Well, that's not fair, but I will tell you what I WILL win".

"When I figure out what it is I want I will tell you, ok?"

"Ok, here's what I will want after tonight" "We have always talked about and fantasized about a 3 way with another guy" Jim interrupts for a second by saying "we've already done that baby" "Hush for a second let me finish, yes we have and thank you, I love you for doing that, but the difference this time being. I want to see you and him playing with each other. He sucks your cock, you suck his, one or both of you taking it up the ass, and I'm getting so wet just thinking about it" 

"Well, that would be an interesting fantasy of yours to fulfill, and the bet was any fantasy we wanted, hmmm, makes me start to think differently about what I want when I win" 

"So, you'll do it WHEN I win?" asks Marsha. 

"IF you should win, a bet is a bet, yes, I will fulfill that fantasy for you baby". 

"Now what did you have in store for tonight so you can lose this bet and I can watch you suck another cock?"

"You're a funny girl baby, all I will say about tonight is, take a nap this afternoon, you'll need the extra rest, shower and shave everything, black dress, no bra or panties. We will get very naughty, and oh, yes I will win tonight". Marsha jumped up out of bed, kissed Jim hard then said, "Oh goodie a play night, let's get some breakfast". After a nice breakfast and an impossibly long afternoon, including a nap where all Marsha could think about was winning the bet and collecting, her mind racing and her pussy dripping thinking of her reward for a bet well made, so she thought. Jim smiled widely watching Marsha getting ready for their date night, knowing what was in store for the love of his life. Shower? Check, shaved? Smooth, Black dress? Check, No bra or panties? Of course not. 

After a wonderful dinner at their favorite restaurant, it was surprise time. "Where we going tonight honey?" 

"Some place we have discussed in the past, and now are finally going to explore" 

"Thanks for clearing that up honey" Marsha said with an overage of sarcasm.

"Do you trust me baby?"

"You know I do Jim"

"Ok, then trust me, I wouldn't let anything happen to you"

"No, no you wouldn't" They pulled up into the driveway of what looked a modest two story house, kind of in the middle of nowhere. "Whose house is this honey?"

With a knowing laugh Jim says "I don't know whose it is, but it is a swingers club on Friday and Saturday nights"

"Really??? You are full of surprises today honey" Marsha said as she gives him a kiss on the cheek.

"Oh wait for the real surprise I promised earlier" Marsha's mind went into overdrive wondering what it could be; she thought this was the surprise. "This is just the beginning", they park the car and head towards the "house". Inside they were welcomed by the hostess for the evening 

"Welcome to Club Sin, there is a $25 per couple cover charge tonight, if you brought anything to drink I will need to check it in here, you will be able to mix your own drinks behind me in the kitchen area"

"Ok, here we just brought this one bottle" Handing over the bottle, the hostess marked with their own membership number and placed it on the kitchen counter. Jim paid the cover charge as the hostess asked if they would like a tour. "Yes she would, I need to make a quick call, and I'll be right back baby"

"Uh, ok, hurry back" Was all she could say as her tour of the club began. The club had just about everything any other club would have, a dance floor with a real DJ, stripper pole, a hot tub out on the patio, but it was small more like a house party, with several rooms upstairs for play. Several other guests were already there, chatting and drinking, getting to know each other, several of them obviously had been there before, greeting each other with hugs and kisses. "Oh this looks like it will be so much fun" Marsha says sneaking up behind Jim and whispering in his ear. 

"I thought you would like it, and you still haven't gotten to the best part yet" Turing to kiss her hard on the lips, his hand running down her ass. "Let go have some fun, your surprise should begin in a couple hours" Her eyes got big, her mind raced thinking what more could he have planned. Back inside, they fixed a drink for each of them, Jim kissed Marsha's check and said "you ready baby? Let's go have some fun" 

"I am more than ready honey, and I am getting so wet right now". On the bottom floor of the club the DJ was pushing out the dance music in one room, the other room had a buffet set out with all sorts of food for the guests. "Oh, you have to go upstairs with me Jim, come on" Upstairs, there was 3 bedrooms, 1 was a private room if you preferred, the other 2 were group rooms with 3 king sized beds in each. They looked into the first two rooms, no one was using either of them, but in the biggest room there was 2 couples lying on one end of the huge play area, both were in a 69.

"Oh can we watch honey?" "Just watch?" "For now" she said with a sly grin. They sat at the other end of bed, drinking and watching the 2 couples, the girls sucking cocks as the guys licked their pussies. "Mmm very nice tongue action on the guy on the left honey, it's making wet watching him eat her pussy" 

"He must be pretty good, she has stopped sucking his cock to enjoy the tongue action he is giving her, bet you would like that tongue in your pussy baby" 

"Yes I would, oh honey, he's licking her ass now, look" 

"Oh I know how you enjoy that, go, see if they have room for more" 

"What are you going to do?" Marsha asked. 

"Watch your sexy ass cum, and then maybe join in with you". Marsha walked to the other end of the bed, "Have room for one more?" "Yes, but you are over dressed" not missing a beat, off came her black dress leaving her naked in front of the 4 some. All 4 stopped briefly watching their newly naked friend climb onto the bed, she crawled up to the guy with the tongue she wanted and slowly slid her wet pussy over his face, and he didn't need to be told twice, his tongue finding every sweet inch of her pussy.

Marsha's eyes closed, head back, she was loving every lick of his very talented tongue. The woman he was eating moved around and started sucking his cock some more. Watching all the action, Jim was getting excited watching Marsha cum all over his face, he moved in behind the girl sucking Mr. Tongue, she looked back and smiled as he dropped to his knees, licking and sucking her clit from behind. 

Marsha heard the woman's moans and sounds of excitement, looking down she saw Jim, smiled knowing the feeling that she was getting from his tongue. She wiggled her ass as Jim licked and sucked harder on her pussy, she pulled the cock from her mouth to say "oh yeah, right there, now I want your cock inside me" Not having to be told twice, Jim dropped his pants, slide a condom onto his hard cock and started to slowly work his cock into her. 

"Oh god, he's so thick, oh my, it feels so good, go slow" Hearing that, Marsha turned around, smiling again, knowing that feeling as well, she slide off Mr. Tongues face, down his chest, rolled a condom onto his cock, and proceeded to slide her pussy onto him, reverse cowgirl. She could control how much of his cock she would take and watch as Jim fucks the woman from behind. Jim was finally full inside her pussy, she had him pause for a couple seconds, getting used to the full feeling. "Oh my, that is a full wonderful feeling, go ahead, but be gentle on me".

Marsha was in full on fuck mode, bouncing up and down on her new cock, watching Jim's cock go in and out of her, she came quickly and very hard, and this sent Mr. Tongue over the edge, his cock contracting inside her, filling the condom. "Thank you" Marsha said, kissing him gently, and then laying on the bed to watch Jim finish. 

"Oh god, oh my god, I'm Cumming" She screamed, Marsha saw Jim's body tense up, she knew he was Cumming himself, she wished it was inside her so she could feel him squirt. She kissed him deeply as his orgasm ended, "Thank you baby, you want to relax in the hot tub before your surprise gets here?" 

"Sure, let me get dressed then we can go relax" 

"Dressed??? Why, just grab your dress and lets head downstairs, we're only going to take the clothes off before we get into the hot tub" 

"Yeah I guess so" they grabbed their clothes, headed downstairs, made new drinks and headed towards the hot tub. 

"I see you're getting the idea" the hostess said as they passed by. Several couples were on the dance floor, one woman was working the stripper pole as if she had done it before. Jim took her clothes, found a place to hang them up as Marsha climbed into the hot tub. He climbed in behind her, his favorite view, slide into the hot water. Cuddling up next to her, she turned, kissed him long and deep "what a great idea honey, the evening has been great so far, this is so relaxing right now"

"Glad you're enjoying everything; the best is yet to come"

"So you say, you gave me very good this morning, still not convinced you can beat that and I'll win the bet, you'll look so sexy sucking cock for me"

"Thanks for the compliments, just relax a little and the real fun will begin" Marsha put her head back, closed her eyes to enjoy the hot water; she didn't see the guy walk in, Jim nodding a hello as he came in. The fun has arrived Jim thought to himself as John walked in. I love it when a plan comes together he thought. 

John walked back out onto the patio area, drink in hand, he said hello to almost everyone there. "He must be a regular" said Marsha, opening her eyes to see what the hellos were all about. Closing her eyes again she tilted her head back and enjoyed the water and Jim's handing rubbing her leg gently like he did in the morning. Jim motioned John over without saying a word.

John stripped down and said "May I join you?" Marsha opened her eyes to see a tall, fairly well built naked man in front of her.

"Baby, he asked if he could join us" Still staring at his flaccid yet still above average sized cock she managed so say "Yes". "Very subtle baby" Jim whispered in her ear with a laugh. She smacked Jim in the arm and said "Hi, I'm Marsha, this Jim"

"I'm John, pleased to meet you" Jim and John shook hands as he sat down in the hot tub next to Marsha. "Is this ok, or do you two want some more room?"

"No, you're ok" said Marsha. Jim closed his eyes, with a sly grin on his face he knew Marsha would get to know him and want to take him upstairs. Jim was barely paying attention to their conversation, but knew based on how Marsha was rubbing his cock, she was doing the same to John. Marsha turned to Jim and whispered in his ear "He has a very big cock honey, can I play with him?"

"Of course you can, as long as I can help too"

"Never without you honey, let's go upstairs" 

"Lead on baby". Marsha stood up from the water, took Jim's hand, put her hand out to John and said "we are going to play upstairs; we would love it if you came with us"

"Thought you would never ask" replied John, grabbing 3 towels Jim handed two to Marsha, and Jim dried himself with the third as he watched Marsha dry John off, especially his cock. John grabbed the towel, and dried Marsha off, only her pussy didn't get any drier. Grabbing the clothes off the hooks they headed upstairs, Marsha in between them. 

Thankfully when they got upstairs, the private room was open, Jim suggesting they use it so it can be just the three of them. Locking the door behind, Jim turned to see Marsha already on her knees sucking John's cock. "Dam girl, couldn't wait huh?" Jim said with a laugh, moving in behind her he started to rub and play with her nipples from behind.

Whispering in her ear "Suck that big hard cock baby, I know he likes that, I love it when you do that to me" Her hands rubbing his balls, slowly licking up and down the shaft of his cock, running her tongue over its head. John's hands grabbed her head, running his fingers through her hair as she sucked his cock. In her ear Jim says, "Let's move to the bed, so I can lick your pussy and ass as you suck that big boy".

Helping her up off the floor and over to the bed, she has John lay on his back and slowly climbs up him to continue her tongue work. Her ass in the air just right so Jim could slide in behind her, sliding his tongue deep into her pussy, licking and sucking her clit. Marsha moans as her tongue traces every inch of John's cock, soon she feels the familiar feeling of Jim's talented tongue slowly sliding into her ass.

She pushes her ass back, trying to get more of his tongue into her ass, her mouth never leaving John's cock. Jim slides up next to Marsha, whispers in her ear "Ride his cock baby, I know you want to, I want to watch you cum on him, then we can play some more" Not needing a second invitation, Marsha slide up John's body rolled a condom onto him and started to lower her wet pussy onto his big thick cock.

Jim sat at the end of the bed watching her work his cock deeper. Slowly stroking his thick cock watching Marsha finally take all of John inside her. 

"Honey, his cock feels so good inside me"

"I see that baby; you look so sexy riding him"

"I see you like it, stroking your hard cock for me, so thick and hard, oh god, he feels so thick inside me" 

"Make him cum baby, squeeze his cock with your pussy" Slowly she begins to grind her pussy on his cock, his balls start to tighten, Jim can see John is about to cum. 

"Yes yes, deeper John, make me cum too" His back arches and he empties himself into the condom, Marsha Cumming with him. She crawls off his cock, kisses John gently "Thank you". 

Kisses Jim hard, "Thank you honey" "I have to clean up, be right back and I'll take care of you honey" 

"Can't wait baby" Marsha exits the room, thinking to herself, that was good, but I'm going to win the bet still. Coming out of the bathroom, Marsha is all smiles thinking she was going to get her fantasy, just when will she ask for it now. Walking back into the room, Marsha stops dead in the doorway, in front of her was Jim on his back, in a 69 with John, both of them sucking each others cocks. 

"Close the door baby, unless you want to share your surprise with everyone else". Without taking her eyes off the action in front of her, Marsha closed and locked the door. Sitting on the edge of the bed, Marsha watched intently as Jim licked and sucked John's cock, John licking and sucking Jim's balls, then his cock. 


A Bet's a Bet



Part 1

Big organizations love to have their national conventions in Orlando. People are more likely to sign up and show up when Disneyland is nearby (don't ask me why) and the whole city is a manicured wonderland with palm trees, waterfronts and plenty of public transportation to get back to your hotel after a binge drinking night with the buddies. "What goes on the road, stays on the road. . ." as any road warrior worth his salt will tell you.

I'd been going to conventions for 15 years, ever since I started working in sales for companies like IBM, HP, and Pfizer. I was heading the sales team for a start-up that had just closed its second round of funding and this Orlando conference was our big coming out launch party. Our product combined social networking, organizational training, and unique content that leap-frogged our competitors and put us 18 months to 3 years ahead of anyone else in the field. In the last 9 months since I'd come on board as senior VP of sales and business development I had racked up 150,000 frequent flier miles. . .not points, MILES. I'd built my team around quality professionals I'd worked with before as well as those who had been with the company from the time of its days in the proverbial garage (in this case the founders' basement). This convention was as much celebration for my team as it was about the sales meetings we'd arranged. The next four days and nights were going to be just as sleepless as the last 9 months had been, but for very different and much more interesting reasons.

This was why I was so excited to get out to the pool party I'd arranged for the sales team on the man-made lake of the Hilton Disney World Resort and Spa. Everyone had flown in earlier this morning and had either been out for a round of golf or spa treatments. Despite the economic tough times we had beaten our pre-launch targets by 250% and the management were falling over themselves to say "thank you" and "don't leave now and give our competitors the golden goose". Everyone was already out by the bar enjoying themselves and I beamed as I walked over.

I could see Gabby -- her big blue eyes unmistakable even at a distance, her fine brunette hair straight and obedient as always, her breasts still ample after her recent pregnancy and on full display with a plunging neckline in her flower-print yellow sundress. Next to her were Becka, Angy, and Tom. Becka was a sales veteran of 25 years with dark red hair, a perpetual Texas tan, and Sally Jesse eye glass frames that commanded the attention of any room she walked into. Angy was still in her twenties, barely 5 feet tall and a roly-poly fireball of blond ambition who owned the Midwest territory and who was looking as mellow as I'd ever seen her after an afternoon massage. Grinning next to the three lovelies was Tom, the 60 year old, steely-eyed, gray-maned former Marine who had followed me from HP and Pfizer to this shot at the big dollars. . .the REALLY big "fuck you" dollars that start-ups used to promise and this one had the chance to actually deliver. He'd gotten in his round of golf and was looking ruddy from the sunshine and no doubt his 3rd drink or so. . .

My attention was on the team and my anticipation was on my first Bombay Sapphire and tonic when I heard my name.

"Randy, hey Randy. . .over here," came the call. Now I'm an easy-going guy on most things, but one thing I make very clear to people, especially people I work with, is that my name is Randall, not Rands, or Ran-man, and sure as shit not Randy. It could only be one person calling me. . .and sure enough it was -- Cally Pines.

Directly in my line of approach to the bar and my mellow, fellow sales-warriors stood Cally with her marketing goons. These were the guys taking credit for our early sales success because of marketing bullshit they'd cobbled together and sent out at random to everybody on some list they got ripped off on from a broker. They always wore the fake smiles of Disney characters -- Goofy comes to mind -- and you had to watch your back for the inevitable knife they were preparing for it. The temperature around me dropped 15 degrees when I realized I had to navigate this snake pit before even getting fortified with a drink.

"Yeah, hey Cally," I said, deadpan. The VC-mandated board members were at the marketing table as well getting all manner of bullshit poured in their ear by Cally's pukes.

"What a great day, huh?" Cally said. "I love Orlando! Did you get in a round this afternoon, the fairways were super-fast."

The saccharine in her expression was making my teeth rot. "I had some customer meetings today, but I know Tom got a round in. I'm heading over to say hello to my team as a matter of fact."

Cally's team were all looking at us, waiting to see what would happen. It was no secret Cally and I didn't see eye to eye on how to bring in customers and how to close deals. She thought glossy postcards and coffee mugs were the way to go when selling executives and my "old-fashioned" view was that relationships and offering solid value was the way to go. I was sooo behind the times.

"That's so great that the whole sales team is here for our launch, you guys are really doing such a fantastic job. Congratulations, I just saw the latest numbers, you guys are really rocking and rolling out there!" I couldn't help but imagine her as a cross between a Disney princess and Barbie -- dirty-blond hair, gray-blue eyes and a plastered-on smile. Cally looked like Tea Leoni would look at 60 though she had just hit 40 the year before. I'm sure she had been a pretty girl when she was younger, but now the wrinkles and worry lines, and the thin, taut skin in the dark circles around her eyes were telling the story of someone in over her head and paddling with all her might just to stay afloat.

There was no love lost between me and her team: Lena, MarComm mistress of the dark who was an odds-on favorite of being a transsexual with her 6'2" frame, baritone voice, and NBA-sized hands; Krystal, the manic PR drone who was so hyper it seemed she would shatter into a million pieces at any moment; and Oswald, the Danish direct-marketing specialist who was the only competent member of the team but was so hen-pecked and dominated by his female colleagues that he came across as spooked and jumpy all the time.

"Okay, thanks for the kudos, um. . .good work on your collateral for the show, it uh. . .yeah, looks really professional. I'm sure customers will really love it." I was doing the act for the board members, Rick Jansen and Angela Cuvier, who had come from other start-ups they had helped to take to the IPO stage and were still getting the measure of the management team.

"Wow, thanks so much Randy, that's really nice of you," gushed Cally.

I nodded at Rick and Angela, "Nice to see you both here. I'd love to get you in front of a couple of customers in the next couple of days if you're available."

"That'd be great, Randall," said Rick. "Angela and I were just talking about how we'd like to sit down with you and really build on your early success. Maybe even learn a thing or two. . ."

Angela nodded and raised her glass, miming a toast, "Nice job, Randall, your team is really firing on all cylinders. Give them all our congratulations and we'll certainly make ourselves available for your customer meetings."

I could see that Cally's smile never wavered, but her eyes had turned cold and dark as a viper's. Ahh yes, I love the smell of corporate politics in the afternoon. . .

"So Randy," called out Cally. "Where are you taking your team for dinner?" She just couldn't let go: if I named some place cheap then I was a miserly boss, but if I was taking my team some place nice then I was a spendthrift. Ever the snake in the grass. Engarde!

"We're heading over to Sam and Delilah's -- it's supposed to be quite a good steakhouse and we don't have to cab it there and back. Gabby suggested it." Generous boss, but conscious of expenses. Riposte!

"Oh that's so cool," Cally gushed, "I love steak. My nickname in college was Cally the Carnivore. I mean I could really put it away: burgers, steak, if it was red meat I'd eat it." And she laughed loud as a hyena on the African plain. Then her team joined in to the yelping and guffawing. To give the devil her due, Cally may have put down the steaks and burgers, but she'd kept her figure into her 40's. But good Lord was she loud and abrasive! I exchanged a look with Rick and Angela as if to say: good luck with this one and received subtle grins in return.

"Okay, see you later, everyone," I said and waved as I made my way to the sales party that was in full swing.

When I got there Tom gave me one of his patented man-crusher handshakes, while Becka and Angy leaned in for European-style kisses on the cheek. Gabby flung her arms open and pulled me in for a bear hug that pressed her large breasts and toned body against me for a good five or ten seconds. My guess was she'd started drinking during her golf round.

"Well hello boss-man!" Gabby declared. "Nice of you to join us, now you've got to catch up because you are REALLLY behind. . . But cuz we know you and love you, we got you started already." And at this she pushed a tumbler full of clear liquid and just a couple of ice cubes in my direction.

"It'd better be Bombay Sapphire in there. . ." I said.

"We KNOW!" they all answered and fell back laughing. I put up my hands by way of resignation -- ya got me.

I raised my glass and said, "A toast: to the best damn sales team I've ever worked with, God bless revenue!"

"God bless revenue!" they all shouted and we clinked our glasses together spilling alcohol all over our hands in the process. That didn't stop us from downing our drinks in nearly one gulp.

Then it was on to another round. And another. . .

As the sun began to set in ochres and purples, and the breezes blew more chilly than refreshing, we headed inside to Sam and Delilah's, the five star steak restaurant at the Resort. Shrimp cocktail, 20 ounce steaks, red wine, more toasts. The night was flying by in the perfect way. We regaled each other with stories of our craziest sales calls, our biggest deals so far, and even to the big scores we were working in the weeks to come. By the time dessert came around we were all red-faced, hoarse from laughing, and on Cloud 9. There'd be a long day full of customers tomorrow, but tonight we were letting it all hang out.

In fact, some of us were letting more hang out than others. Becka had undone her trademark maroon jacket and it was hard not to stare at her D-cups straining at the silk blouse underneath. She may have been over 50 but she had a solid rack and firm skin. I kept having to snap my attention back to the conversation after my gaze would sweep over her cleavage.

Angy also had loosened up, taken her hair down where it hung past her shoulders, and kept hopping up and down during her stories making her own young, firm boobs jiggle noticeably. I could tell that Tom, for all his military-style presence, was having a hard time keeping his eyes off the girl who was younger than all three of his daughters.

The other thing I couldn't help but notice was Gabby, who was sitting to my right, occasionally rubbing her arm or her thigh against me. Or leaning way over to her left during a toast so her breast was practically falling into my plate. She would also give me playful punches on the arm whenever I'd get to the end of my stories. Yeah, there was definitely something going on there. . .

But that was the whole point of getting together away from headquarters, away from families, and without quotas or deadlines for these four days -- to let loose, flirt a little, drink a lot, create some personal connections and come out of it with enough momentum and excitement to tackle the next 9 months as the company barreled towards its IPO or acquisition.

We ordered dessert for the table, a chocolate soufflé bread pudding that gave you diabetes just looking at it. They brought five spoons, but I opted for a nice little dessert wine, Moscato d'Asti, to let the flavor of the top grade beef linger on my palate. The girls were having none of that! While Angy and Becka fed each other the soufflé from their long spoons with Tom looking on open-mouthed, Gabby insisted that I try the "oh my God this is just GORGEOUS!" dessert. She dug into the gooey center of the concoction and brought a heaping spoonful to my mouth. I opened wide and she slid it inside gently, almost tenderly. When a stray drop of chocolate escaped past my lips and down my chin, Gabby scooped it up with her index finger and licked it all up.

"Good huh?" Gabby asked, looking into my eyes.

"Hell yeah, but I bet it was better licking it off your finger," I said, a bit surprised at myself for going along with the flirtation. As much as I think that sexual harassment is pure bullshit, the last thing I'd wanted to do it screw up the dynamics of my sales team and get Gabby's head all turned around about her marriage, especially with a new baby at home.

But, damn, those blue eyes were magnetic, like tractor beams pulling me towards her. She had a freshness and energy about her that I always liked and that helped me hire her. Those qualities no doubt were a big part of her sales success. People like to buy from people they liked, and everybody liked Gabby. Her sundress showed off a few inches of cleavage; she'd had modest breasts before the pregnancy and it looked like she was proud to show off her new plus-sized tits (and no surgery!). Though the hem of the sundress ended below the knee it was easy to see she had been getting off the baby weight by exercising as her calves and the stray flash of thigh were muscled and toned. The fact that she had spent the night rubbing those legs and her arms against me wasn't helping either.

Still, we were just having some fun right?

After I paid the check, Angy had a brainstorm: let's all go to the club lounge in the Hilton, called Sunstar. The other gals loved the idea and pulled me and Tom by the hand all they way across the lobby and into the club. They played techno and club music and Sunstar was packed. Becka and Angy pulled Tom over to the bar saying they'd be getting us all drinks while Gabby pulled and pushed me onto the dance floor.

Dancing hadn't been my thing for a long time, since I'd gone out partying most nights while getting my MBA, but the motions and rhythm came back to me pretty quickly. It helped that Gabby was gyrating and grinding her way all around me. She would pull herself close and shimmy down to the floor stopping just as her face was level with my crotch. Then she'd do the same thing in the back and give my ass a squeeze.

I leaned into her and said through the din, "Two can play that game."

"I double-dog dare you," she laughed back at me.

We kept dancing but my eyes locked in on hers for those few extra moments that said, "Oh yeah, it's on!"

I moved closer to Gabby and put my hands on her hips. They were soft but firm with muscle. Giving me a smirk and with her eyes looking into mine, Gabby moved closer until our bodies were touching all while wiggling her hips to the beat against me. I spun her around with my hands so instead of facing me my body pressed against her back. Her full, firm ass pressed right against my hardening cock. I didn't even realize I was getting hard until Gabby pressed her ass against me and started to really grind it against my cock. She arched her back and wrapped her left arm around my neck as we swung around the dance floor. My hands moved just a couple of inches below her hips to knead her ass cheeks. My cock got harder and harder with every beat.

Front-to-back, and front-to-front we kept dirty dancing together for another few minutes until Becka, Angy and Tom brought our drinks.

"Cool down you too, pace your dirty selves!" laughed Angy. We grabbed the drinks and toasted again.

"To a great night with good friends," said Tom. Everyone echoed, "Cheers!" and down went another round.

What I hadn't noticed was that someone had brought along a tray of shots and now that we'd down another round they were passing around these small glasses with a pale gold liquid in them.

"There's NO way we're doing shots," I protested.

Becka slapped me on the arm, "Go on now, Randall, I've got 20 years on you and if I'm still drinkin', you're still drinkin'!" Then the shot was pressed into my hand and Gabby said the toast, "No rest for the wicked!" In one gulp the shots were gone: sweet like honey with a fantastic kick like getting rear-ended by a semi.

"What the hell was THAT?" I coughed and sputtered when I regained my breath.

"Oh, that's potchian," said Angy, "my boyfriend introduced me to it when we went to Ireland last year. It's strong huh?"

Everyone nodded and then we got back to dancing. It was almost impossible to hear each other in the club so we flowed in and out of dancing with one another and in a big group. After another shot of potchian however, Tom and Angy paired up and disappeared into the crowd and Becka winked at me and grabbed a guy who looked to be in his 20's and began throwing all her moves at him. He just smiled and went with it.

Gabby and I were alone and red-faced and sweaty in the crowd. She pointed for us to head off the dance floor and into the slightly quieter lounge area. I grabbed her hand and made our way through the crush of dancers and on-lookers.

When we got to the lounge and sat down for a minute, Gabby said, "I hate to do this, Randall, but I've got to head back to my room -- I'm exhausted and pretty drunk." I could see she was right: there were dark circles under her eyes and her cheeks were glowing a nuclear pink.

"Yeah, that's probably the right move," I said back in her ear. "It's been a long night and we've got three more just like it ahead of us coming up." As I talked to her I could smell her floral perfume and the clean smell of her hair, along with her dance sweat and the pheromonal tang of arousal -- it was more intoxicating than the potchian. "I'll walk you to your room, drunky."

Gabby laughed, "Okay, Mr. Sober."

We made our way out of the club and through the lobby of the hotel back to the elevators. As we waited for the elevator I had my arm around Gabby's waist and she had her hand on mine. It was very casual, relaxed. I could feel the throb of my cock from our earlier dancing, but I was keeping my breathing deep and even. Gabby settled her weight against me and sighed a little.

When the elevator arrived we stepped into and I pushed 17, Gabby's floor. "You're a really good dancer," she said, breaking our mutual silence.

"Well thank you, you're pretty good yourself. I haven't danced that much since B-school."

She looked mischievously at me and said, "Oh, you were dancing pretty hard alright."

As flushed as I was, I'm sure I turned several deeper shades of red at that comment. "Hey, that was all your fault you know. Tossing that ass around. . . I'm just a man after all, not a wooden statue."

"There was plenty of wood on that dance floor," she kept mocking me as she leaned her body against me. I couldn't decide if I wanted the elevator to speed up or slow down. I could feel her body through her dress brush against me and my cock was reacting just as it had on the dance floor.

"Feels like you know your way around the hard wood," was all I could think of. I had thrown myself into this job after my divorce five years ago and besides the odd fix-up from friends or a celebratory strip club outing with the guys I really didn't do a lot of sex. . .anything! So here I was in a hotel elevator getting hit on by a work colleague who was a subordinate and married, and I was completely out of practice of feeling this horny around a woman. Every Michael Douglass movie I'd ever seen with dangerous women flashed in my mind -- Glenn Close, Sharon Stone, Demi Moore -- but it did nothing to cool my blood or ease my hard-on.




A Bet's a Bet



"Mmmm, I sure do know good wood when I see it," purred Gabby and ran her hand down my crotch and over my stiff cock. Then she gasped and looked at me surprised, "God Randall, I suspected you were packing, but that's a Louisville Slugger in there!"

The only thing that gave me a reprieve, however momentary, was the elevator gliding to a halt and the doors sliding open.

"Walk me to my room?" Gabby smiled at me wickedly. I just nodded and followed.

She led me by the hand to her room which was in a small alcove at the end of the corridor. She reached into her purse for the electronic key, but then without warning whipped around and grabbed my neck with one hand and my cock with the other and planted a wet, drunk kiss on me just to the left of my lips. She tasted of alcohol and sweat, and a citrusy lotion, musky perfume, and the effulgent glow of trangressive need. An irresistible cocktail.

My body reacted for me: I answered her kiss with my tongue, exploring her mouth and tongue with my own; I pressed her against the door of her room and myself against her, my manhood insistent and hard against her belly; my hands slid down to her hips to keep her against me; I felt her nipples stiffen against my chest as our bodies flowed against each other. Our kiss lasted long minutes, or it could have been the whole night.

Finally I broke our connection. "Good night," I rasped.

Gabby looked at me with eyes glazed over with arousal and desire. "Mmmm, it could be an even better night. . ." She let that hang in the air between us as she fished out her key and waved it hypnotically before me.

I wanted to go into her room more than I'd wanted anything in a long time, but I wanted a small bit of sanity and self-respect more. I didn't know if I still had any left of either, but I'd check after a freezing cold shower in my room.

"Let's pace ourselves, get some sleep. . . Good things come to those who wait." Still weak, but my brain wasn't getting most of my blood at the moment.

"Good things coming. . .you're quite the dirty one aren't you. . ." Gabby said, and then she laughed. "I'll see you again after I get some sleep, don't think you're off the hook, boss-man." And she pulled me in for another hug. "Not off the hook by a long-shot," she whispered. I kissed her cheek and she stepped into her room.

The door clicked and the last thing I saw were her blue eyes staring at me, daring me. Double-dog daring me. I stood at her door for a couple of minutes, smiled to myself wondering if she was looking at me through the peephole, then I turned and walked back to the elevator.

Part 2

Luckily my wait for the elevator was brief and I didn't have to share the elevator with anyone wondering what the hell I was doing sporting a raging hard-on, sweaty and reeking of alcohol. I exited on 24, my floor, and as calmly as possible, made my way back to my room. Which was where my luck ran out.

The door next to my room was open and Cally Pines was standing in the doorway laughing and flirting with Rick Jansen. Rick looked half in the bag himself, had his suit jacket thrown over one shoulder and was leaning on the door jamb. Cally, incredibly, was wearing only a button down Oxford shirt and, as far as I could tell, nothing else! Her legs were pale and spotted with freckles, but they were certainly one of her best features -- firm, muscled, long. Her feet were broad and spade-like, with the toenails painted a dark, brick red color.

I tried to just nod an acknowledgement to them and to slip into my room, but my door was literally right next to Cally's door. "Who the hell designed this damn hotel?" I thought angrily to myself. "And why the hell do I have a raging hard-on and my card key isn't working while I'm getting more aroused by Cally's legs and Rick is looking at me blearily and with visible discomfort?! I can't save everybody, buddy!"

"Hi Randy," chirped Cally. "How was your night with the sales team? Bet you guys had a lot of fun. Did you go out after dinner?" I could swear her gaze was locked in on my crotch while she was talking.

Good Lord she was nosy, "Had a great time, and then made our way to Sunstorm, you should check it out," I said. 'You should check it out'? what the hell was coming out of my mouth? 'Just get in the door, Randall, nice and easy, smooth and simple. . .'

"Randall," said Rick.

"Rick," I said. "Good night you two, see you bright and early."

"G'night Randy," crowed Cally.

And then the door lock clicked and the door was open and I shot into my room and pushed it shut behind me as fast as I could. 'Great timing, Randy,' I thought to myself. 'Anyone else you'd like to show your hard-on to tonight? Anyone? Maybe Becka and Angy didn't get a good enough look at the club. . . Maybe Tom wants to have a competition about old guys getting hard-ons with younger girls? Idiot!'

But there was no use now wishing I had stayed with Gabby, or wishing I had calmed down my cock before heading upstairs. . . It was time for that cold shower and some sleep. I kicked off my shoes into the closet and stripped off my pants and shirt into my laundry bag. The cold water was bracing and got my blood pumping somewhere other than my loins for a change. My brain was finally starting to work again. My body was cooling down and sense was returning, however slowly, to the rest of me. I wasn't worried about Gabby being hurt or "weird" the next day, the only thing I was thinking about was what the hell I meant about us "pacing ourselves." Was that some kind of implicit promise of. . . what. . .sex? I really needed to get out more.

I'd dragged a brush through my hair and was winding down my speculation for the night when I heard a knock at my door. Who the hell could that be . . . at 2 in the morning, in Orlando. . .? The night was getting weirder and weirder.

Instinctively I grabbed a towel and held it around my hips as though someone could see me through the door. I peeked through the peephole and called out, "Who is it?"

The sight and the answer came at the same time: it was Cally. "It's me, Cally," came the slightly sing-song, slurred reply.

Just when I didn't think the night could not get any stranger and out of control, there she was -- the queen of loud and the princess of cheesy.

"It's a little late, Cally. . .are you locked out?"

"No, it's just. . .well, can I come in? I kind of need to borrow something."

"Cally, come on, it's 2 in the morning, ya want to just grab some sleep?"

'Kind of need to borrow' -- the quintessential weasel phrase -- as little information as possible as blandly as possible, no doubt meaning she needed to take something pretty expensive and important. At 2 in the morning. . .in Orlando. . .and me standing there with just an over-sized hand towel covering my goods. But I'd be damned if I was going to get dressed and be put out because some drunken, corporate climber needed a power cord for her Crackberry, or whatever the hell she wanted.

Neither of us said anything for a long minute.

"Please," she paused, "Randall, if you let me in I'll let you in on a secret. You'll like it, I promise."

A friend of mine grew up on the East Coast, in Philly. He would tell me that during winter the biggest danger to drivers wasn't the snow or even rain, but black ice -- water that had frozen and re-frozen so flat and slick that you couldn't even see it. When a novice driver hit black ice and started to skid inevitably he would yank the steering wheel of his car in the opposite direction of the skid in order to regain control and to "get his wheels back under him". This was exactly the wrong thing to do as the over-correction produced a fish-tailing vehicle out of control and careening dangerously across the road. What experienced drivers had trained themselves to do was to 'steer into the skid' -- to turn the wheel in the direction the black ice had thrown them in order to use the car's momentum to get them through the frictionless surface and onto safe ground. Only by doing this could you minimize the damage of hitting black ice and increase your chances of getting back on the road in one piece.

My friend and I had adopted this term -- 'steering into the skid' -- to acknowledge that sometimes when a situation at work or in personal life hit unexpected bumps and left you feeling out of control, despite wanting to fight for the control, instead the best thing to do was to let go and go with the flow. To steer into the skid. That way damage was minimized and you could regain control much faster. At least that was the theory. . .which I was now in the process of testing in my hotel room engirdled only by a hotel towel.

With one hand holding the towel in a firm grip around my nethers, I opened the door with my other hand. "Sure, Cally, come on in. . .what can I do for you. . ."

Cally made her way into my room and leaned against the door to close it. She was still wearing the button down blue Oxford that made it look like there was nothing underneath. I also noticed that the shirt was unbuttoned down to her solar plexus and that her nipples were hard points protruding through the cotton weave of that shirt. Unfortunately I also noticed that her breasts were larger than I had ever guessed. Without a bra they fell 5 or 6 inches lower than I was used to seeing in the office. She was easily a D-cup with an impressively flat belly above those long, toned legs. Noticing all this was quite unfortunate because the erection that the cold water had worked so well at counteracting, the sight of Cally had enflamed anew. The inadequate towel grew only more inadequate by the moment.

"So. . .," I started, "what, uh. . .can I do for you? You said you needed to borrow something?"

"Hmmm. . .," Cally paused and I could see her looking me up and down, mostly down. "Well, Rick was over and we kinda went through all my little bottles of Jack. And all the Cokes. . ." She giggled. "Now he's gone and I could use a little nightcap for the road, ya know?" Then she smiled. It may have been the first genuine smile I'd seen on her. One without calculation spinning in the difference engine in her hominid cranium. Not that I was going to turn my back on her for a second, but clearly tonight was having its eerie effects on everyone.

"Help yourself, my mini-bar is over by the TV," I motioned with my free hand over to the 50" LCD screen hanging on the opposite wall.

"Cool, thanks," said Cally and wagged her hips all the way across the room. I watched her pad across the room barefooted and couldn't see an outline of underwear under that shirt, but it was just long enough to not show off even a flash of ass cheek either. Blood thundered in my ears as I wondered how she was going to get her drinks from the little mini-bar set down low on the floor.

I found out right away: Cally got on her knees and wiggled her ass as she cleaned out my stock of tiny liquor bottles -- Jack Daniels, Southern Comfort, Tanqueray. . .pretty much everything in there.

"Those are coming out of the marketing budget," I said. When she turned around I could see she had snagged over $100 of mini-booze from my fridge.

"Relax, Randall, I'm always good to my friends," purred Cally. "And anyone who lets me into his room at 2 in the morning to snag booze is a *good* friend of mine."

She had gotten up off the floor with her boozy booty clutched to her chest pulling her shirt up another couple of inches up her thighs. I was glad that booze was all she needed because her body was sexy and having no uncertain effect on me. Even sitting on the bed and hiding my re-awakened cock I wasn't going to be able to keep it to myself for long. I needed privacy and soon to keep my interest under wraps.

"Okay, that's great, Cally. Enjoy your nightcap; I'll see you tomorrow at the show."

She pouted for a moment, "Aren't you going to have a quick drink with me, Randall?"

That was the second time she had called me Randall. She definitely wanted something, but this was no time to be building bridges. "I'll take a raincheck, thanks. I need the rest. Good night, Cally."

Never underestimate the power of a good silence. Cally knew she had been dismissed and after a few moments of quiet she moved towards the door. When she was just a foot or so from the handle, she turned back, "Aren't you curious about my secret, Randall?"

Almost free. "Why don't you tell me tomorrow. I'm sure the sales numbers or web pages responses will keep till then."

"Oh, it's got nothing to do with marketing, this is a private little piece of information. I think you'll enjoy it."

Good Lord this woman was getting on my last nerve. I could see how she had gotten to be VP of marketing -- stamina and persistence. Steer into the skid. . .

"Okay, sure, go ahead: tell me your secret."

Cally put her little bottles down on the dresser by the door and came back to sit in the armchair across from the bed. Me in my towel and her in the button-down, great examples of two professionals having a meeting.

She began, "You know how I tell people that I used to be called Cally the Carnivore because I eat so much meat?" I nodded. "Well, that's not how I got the nickname."

With this she put her feet on the floor and spread her legs a little. Another inch or two and I'd be staring right at her cooch. Just for a moment I wondered if she kept it natural, trimmed or shaved. I said nothing.

"My sorority sisters gave me that nickname, actually," Cally continued. "During my initiation they made me the 'coat check girl'. I thought the point was for me to dress slutty and take everyone's coat, but there was a lot more to it. To get into the house I had to suck off all the guys who came to 'check their coats.' And there were a lot of guys at that party. Sometimes two guys checked their coats at once."

Cally kept talking, but I couldn't really hear what she said. My heart hammering in my chest and the blood thundering through my ears drowned her out. All I could think about was this cute co-ed with her dirty blond hair and big blue eyes sucking off one frat guy after another, taking two cocks at a time. . . There was nothing I could do about my raging hard-on now, it was champing at the bit and the towel was a silly little attempt at modesty.

The next thing I heard was, ". . .and I couldn't even wipe my face the whole night. I was covered in cum till everybody left. The next morning I got my house invitation and my new nickname -- Cally the Carnivore." Now she sat silent, looking at me. . .double dog daring me to keep quiet.

"That's some story, Cally," I stammered. "College must have been quite the adventure for you."

She laughed, an easy laugh that was both giddy and world-weary. "Yeah, definitely an adventure. Every frat guy heard about my initiation and was getting me drunk so I would blow him. I guess one thing I got out of the whole thing was being great at giving head, there isn't a cock I can't deepthroat, and I've had more than my share."

Now she looked at me defiantly, waiting for me to challenge her cocksucking expertise. Leaning forward to give me a better view of her full tits. You doubt me, buddy? her posture said.

What I should have done is thanked her for the story and pointed her to the door reminding her of the hour. And maybe it was some kind of pent-up need or singularly clever devil who sprang to my tongue that moment, but what I actually said was, "That's definitely impressive, but no one has ever come close to deep-throating my cock. Not even close."

As soon as the words came out of my mouth I wanted to take them back, but you can't put the genie back in the bottle.

"Is that a challenge, Randall?" smirked Cally. She stood up and came closer to the bed. "You must have some kind of massive cock hiding under that towel. ..or maybe the girls you've been with weren't good at giving head."

As she came to stand right in front of me, she undid the last few buttons of her shirt and let it slip to the floor. "So you want to let me try?"

For all the political corporate bullshit that our relationship had been built on, my dislike for Cally did not blind me to her beautiful full tits, hard brown nipples, and worked out body. I also had the answer to the question that had popped into my head earlier: she was trimmed. I looked up at her challenging smirk, having completely lost control and now sliding on the black ice of co-worker sex, and said, "Sure, let's see what you've got."

Before I got the towel off me, Cally chimed in, "So what do I get if I win? Let's make this interesting." She had the body of a sorority girl, but the brain of a frat jock.

"Okay, let's make this. . .interesting then, but no work bets, let's make this personal," I offered.

She nodded, "Personal it is." We both thought for a minute then Cally's eyes lit up. "I got it: if I can deepthroat your cock, I mean really tongue your balls with your cock deep in my throat, you have to eat my ass. That personal enough for you, Randall?"

As she turned around to show me her ass, I could see that it had definitely gotten bigger since her college days, but was nevertheless firm and with no cellulite. I was never a big ass-eater, but what the hell, it'd be worth it to finally get some deepthroat head.

"You're on, I'll eat your ass if you can deepthroat me, but if you can't then. . .I get to fuck your ass. You game for that?" No one had ever let me assfuck them before, not drunk girls in college, not my wife of almost 20 years, not even any strip club girls after a crazy night of drinks and speed. But this was the art of negotiation -- win-win, mostly for me.

Cally hesitated. The stakes had gotten way higher than she imagined they would. ..but she laughed it off certain that she win this bet, "You're on, Randall. There's no way you'll be fucking my ass."

At this I pulled off my towel and dropped it to the floor. I guess I thought she would just drop to her knees and start sucking my cock, but she actually took a step back and swallowed hard.

"Jesus Christ, Randall, that's some fucking cock you've got there," she said, her eyes wide.

I'd heard similar exclamations from nearly all the women I'd been with. Not that the number was that great, but still, I mostly put it down to womanly flattery and a desire to get me aroused. I figured most guys heard "oooh, you're so big" like most girls heard "you're so pretty." A polite prelude to sex; an "I'm okay, you're okay" declaration to oil the socio-sexual machinery. With Cally, after her story of sucking dozens of cocks, was the first time I believed that what I was packing was more than average. It wasn't just the length either, I knew the girth was something that challenged some of the women I'd been with even for vaginal sex. Most loved it, but for some it turned out to be just too big.

"A bet's a bet," was all I said.

"I've had bigger," Cally huffed. Then she got on her knees and put her hands on my stiffening cock.

For all her posturing and boldness, Cally really did know how to handle a cock. Her hands moved up and down my shaft and rubbed my head gently getting my fully hard. She worked on my balls and licked nearly down to my ass. From all the teasing tonight, and the drinking, the dancing, the making out with Gabby, the tension with Cally and her revelation. . .my cock was raging hard. And Cally was using all her skills, working her way up and down the shaft of my cock, sucking on my head, working her throat open to take my girth and my thick head down her throat.

After 10 minutes she grabbed one of the little bottles of Jack and downed it in one gulp, all while stroking my cock with her left hand.

"Fuck, Randall, if I'd known you had this massive cock I would have come on to you months ago. You've got the thickest cock I've ever had."

"You're a goddam pro at sucking cock, Cally, I don't mind telling you. Really, nobody's ever worked my cock like you, but you've only gotten about halfway down. . .so. . ."




A Bet's a Bet



She attacked my cock with a new vigor. It felt as though she was impaling her throat on my cock over and over. Her mouth and tongue and her hands felt amazing running up and down my cock and over my balls. Without thinking about it, I leaned over and played with her tits. They felt smooth and warm in my hands as I kneaded them and pinched the nipples. I heard her moan at that.

"Please, play with my tits, it gets me so fucking hot, put your hands on my body," Cally moaned and pleaded.

I squeezed her tits harder and let my hands roam over her freckled back and over her ass cheeks. As she gagged, I could tell Cally was inching closer down the shaft of my cock. She was playing with my balls and I realized she was trying to pull them closer to her mouth. Trouble was for all my cock, I've got barely any scrotum, it's a tight package at the base of my cock that melds seamlessly into my perineum, the taint.

After 20 minutes, I was getting ready to cum, I could barely hold on. "Concede yet, Cally?"

She took her mouth off my cock and looked at me. "Randall, fuck my throat, get your cock down my throat, even if I gag keep fucking me, I can't take that cock in my ass. Please fuck my throat. . ."

Her pleading tripped a new switch in me, a place I didn't know existed. I stood up and grabbed her head in my hands, I drove my hips back and forth, my cock sliding in and out of her mouth and throat. I'd never fucked my wife's throat like this, our lovemaking was too personal and intimate for that. Even the strippers never threw themselves at my cock like Cally was doing. I *wanted* her to take my cock past her gagging point. Without reservation I fucked her throat like the drunken, heedless idiot I turned into.

And still, no matter how hard I fucked her, past her natural limits and the gag-spittle that poured from her mouth, her tongue couldn't reach my balls. The harder I tried fucking her the closer I was to cumming. All of a sudden I went over the edge, I was going to cum and no force on earth could stop me. I kept fucking Cally's throat and hearing her gag made me lose final control. . .

Without pulling out I came stroke after stroke down her throat. She choked and sputtered. I felt the great spurts of semen launch into her. Some she swallowed but a lot she choked out to let it run down her cheeks and chin to mix with her spit and. ..were those tears running down her cheeks?

It was probably no more than 30 seconds, but I felt like I came down Cally's throat for a long time. When no more spasms wracked my cock and my hips, I pulled my slick shiny cock out of her throat.

Cally's face was wet from tears, spit, and my cum. She was breathing hard, catching her breath. I sat on the bed with my cock dripping juices onto the carpet and watching Cally's breasts heave up and down as she caught her breath. The towel was on the floor where I had let it drop and Cally pulled it over to wipe her face clean. Once she had cleaned herself, she crawled over and wiped my cock clean.

Looking up at me she said, "That was the thickest cock I've every sucked, Randall. You should have warned me."

With all the tension having shot out of me with my ejaculation, I laughed at that, "I *did* warn you!"

"I guess you're right, I should have listened," she admitted. "It's lucky for me you came, so you can't collect on our bet," she added slyly.

"Oh Cally, you'll want to grab another couple of those little bottles, because I can cum half a dozen times a night and I'm just getting started."

"Come on, Randy," she whined.

"First of all, that 'Randall', is that clear?"

She gulped, "Sorry, yes, Randall."

"And second of all," I began, then paused. My phone was lying nearby on the night stand. I reached over to it and pulled it over. Cally gave me a quizzical look. Until I brought up the phone and snapped a picture of her sitting naked on my hotel room floor.

"What the. . .what are you doing?"

"Second of all, what would your husband think if he got a photo of you in another man's room with tonight's time stamp? Pretty awkward conversation, right?"

She sat there dumbfounded. "Are you fucking *blackmailing* me?"

"Oh the picture? That's just for my personal use, for posterity, you know. I just know how unreliable digital technology can be with hacking and email piracy."

"Randall, please. . .," the situation was starting to sink in.

"I don't want to make any trouble for you, Cally, but I do want to fuck that ass of yours. A bet's a bet, right?"

She looked down at my cock that was already half hard again from just the past couple of minutes.

"And if I let you fuck me, then. . .we're cool, right?"

"Of course, I always honor my word," I held up my hand in a "scout's honor" salute.

Part 3

There was a moment of calm. What began as a sexual game had turned much more sexual and suddenly, for Cally, much more serious. She couldn't have imagined losing that bet and getting her ass fucked but a cock that wouldn't even fit down her well-used throat. Now she was on the brink of a co-worker who had her on camera naked in his hotel room readying to blast her tight asshole with his outsized cock. It didn't take much of my imagination to understand her confused, tired, and scared position.

And while the better angels of my nature wanted to let her off the hook, the pent up devils of frustration having had to put up with her company political bullshit made me want to collect on my bet. I wasn't going to be heartless about it though.

"Hey Cally, what do you say to us fucking first? It'll relax you and I bet you like your ass played with anyway."

She looked at my flaccid though still thick cock hanging down my thigh and, I couldn't believe this, smiled a little at me.

"Since I saw that fat cock, Randall, I've been hoping you'd fuck me with it. Do me from behind too, like a bitch at your cock, fuck me deep. That'll get me crazy. . .maybe enough to let you break my asshole." There was both greed and fear playing across her face.

I stepped across to wear Cally sat on the floor and lifted her up to sit on the bed. Feeling her skin on my fingertips, smelling her sweaty and fragrant hair, I couldn't help myself -- I leaned down and kissed her mouth. Tasted her salty, sweet breath, like honey roasted nuts. Cally tasted good, and smelled both of sex and of exertion. My cock stirred again thrilling for what was to come.

Either by instinct or need, Cally's hands stroked my cock as we made out on the hotel room bedspread. She worked it across her chest and her hard nipples. Her moans excited me and I became harder and thicker in her hands. Moaning louder now, Cally reached one hand down between her legs and slipped two fingers inside her well-maintained pussy. Into my mouth she breathed the words, "God fuck yes, gimme that huge cock, Randall." She was calling me 'Randall' now and I liked the sound of her compliance.

Then the fingers of her right hand were on my cock slathering it with her pussy juice. She covered my throbbing head and stiff shaft running her fingers up and down. Our tongues were insistent and urgent now, probing and thrusting deep into each others mouths. As much as I enjoyed the feel of her mouth on mine and her hands anointing my cock with her sacred nectar, I needed to fuck her and NOW.

My hands were on her shoulders and I pushed her back on the bed. She looked at me with eyes ablaze with a dark hunger, a deep unfillable need that illicit danger and hyper-sensory experience could temporarily satisfy. I grabbed her thighs and moved her legs higher and wider apart; then my hands were on her ankles, she was on her back on the bed and her ass barely supported at the edge of the mattress.

She began to say something, "I need more sup. . .", but she never finished, I pulled her legs up a little and thrust my cock inside her wet cunt. Not all the way at first, just the thick head and an inch or two of the shaft to feel her warm wetness on me.

"Ahhh,. . .God, ahhhh," Cally stifled a scream and moaned like a wild animal. "Holy shit, god, please. . .oh shit, Randall, fuck that's too big. . ."

Those sounded like pleas to stop, or at least slow down, but not to the primitive, reptilian part of my brain that ruled me now. To that muck-dwelling survivor of a thousand challenges to its being these sobs and squeals were red meat and meant it would feed and live another day. I got harder, my cock grew thicker and slide further into Cally's drenched and hot pussy.

I looked down at Cally and her eyes stared back at me. The eyes that looked back at me were not the scheming, Machiavellian eyes of a co-worker or ladder-climber, but the eyes of a rutting beast both joyful and challenged at the new boundaries of its existence. She was being stretched wide, and she loved it, and still some small warning klaxon of self-preservation bleated in her brain that this thing invading her, this cock that was bringing her pleasure, would soon likely ram itself, perhaps somewhat slowly but more likely with an undeniable force, into her all-but-virgin ass. This combination of pleasure and fear drove Cally's human niceties from the field and looked out from her yes like a Fury that would have its justice. At another time I would be scared in my guts from a look like that, but at that very moment I reveled in the raw state that was as natural for me as breathing.

"Fuck me like a bitch, Randall, turn me over and fuck me deep," Cally pleaded.

Without a though I grabbed her hips and swilled her with my cock still embedded in her. She grunted and her sweat was on my hands. Freckles and droplets of sweat covered her ass and her back. Now my hands were on her ass and spreading her cheeks wide. My cock drove deeper and deeper into her pussy.

"Stop, goddam it, fuck please just stop!" she begged. I stilled for a minute with my cock deep in her pussy, about three quarters of the way in. Just a couple inches of my cock were still visible. I didn't say a word. Just stayed still with the veins in my cock throbbing with blood.

"Okay, okay, damnit, I've gotta catch my breath, shit," Cally gulped air. "Fuck, Randy, you are stretching my pussy. . ." She didn't get the chance to finish.

The word "Randy" erased all conscious forebearance from my brain; I slammed the rest of my cock into Cally's pussy.

"Oh God, ahhhhhh, shit, sorry sorry," she sobbed.

I slid my cock out slowly, an inch at a time, as she exhaled and was about to take another breath, I slammed it back inside her.

"Ow, fuck, oh God, Randall, Randall," Cally's voice was cracking and squeaking.

I fucked her steady now, the rhythm of a piston in a recalcitrant housing, in then out, out then in, again and again. . .

"Oh holy God, oh fucking yes, please keep going, fuck me fuck me fuck me hard!" she spit and snapped into the bed spread. I was only too happy to oblige.

For one minute, then two, then three, I kept fucking her from behind. Her head buried in the bedspread, her hair wet from sweat and effort, her pussy red-raw from being stretched and abused, her back still a cello of skin over muscle and bone -- elegant, smooth, peerless. Cally's breathing was steady now and an electric purr rumbled from her throat and pulsed through her body.

We had settled into a brutal but welcome rhythm, Cally's moans came out almost satisfied, maybe even relieved -- some need was being satisfied that she hadn't been entirely aware of, couldn't have articulated, but here it was, a space that was empty being filled, a void being put right, and leaving a sense of deep happiness, the consummation of an unnamed but persistent urge. She was in a trance of hot and inescapable satisfaction.

My hands were on Cally's ass, slowly spreading her cheeks apart and working my slick fingers around the hole. She jumped a little away from me at that moment and I grabbed her hips and pulled them deeper on my cock.

"Ugh," she moaned and complied with my unspoken command.

My slick pinky worked its way around her asshole, then slowly inside. This was not her first rodea and she even relaxed her ass onto my little finger, this was a welcome and expected anal assault. I followed the little finger with my middle finger and worked it a bit deeper into her ass. As my cock fucker her pussy, my finger fucked her ass and I could feel my cock moving inside her, rubbing and pounding its way into her depths. Then it was time for two fingers. . .Cally jumped again and was rewarded with another slam of my cock to the bottom of her cunt.

"Oh fuck, Randall, God, you are a making me crazy," she breathed. "Yes, yes, just fucking do it to me, just fucking do it. . ."

I slipped three fingers into her ass now. She controlled her instinct to jump and began to pump her own pussy against my cock now. Cally was beginning to drive herself into a frenzy of orgasm. She wanted to cum now, she was losing herself to her body, to urges more ancient than consciousness, needs that were chthonic and essential to identity. We had to wear masks to hide from one another day to day, we dared not show our true faces, but here in this Orlando hotel room, drunk, and horny, and beyond the pleasantries of the real world, Cally and I were creatures out of Eden: barely named by God or Adam, pure existence the fulfilled the most basic and the most profound needs. And we were fucking, we were moving together, we were beyond any "no" or any "yes", now we were unstoppable.

As Cally pushed herself beyond rationale awareness again and again onto my cock, I slipped my cock out of her pussy, and slipped three wet fingers in. She moaned but didn't let up her pace. My cock was massive even to my eyes now, rock hard, not angry but redolent of musk -- my own sweat and Cally's cunt juices -- and fully in command. It slipped easily between the cheeks of her ass. Back and forth between her ass cheeks as my fingers fucked her pussy.

Almost gently I moved my cock head against her asshole. Her intake of breath told me she was ready, but she didn't jump. I moved it into her ass.

A sharp in-take of breath, "Ahh, ohhh, okay okay, yes," she mouthed and kept fucking my fingers.

Slowly and inexorable I slipped my cock head into her ass. Cally just grunted and drooled, I could see spittle leak from the corner of her mouth.

"Oh fuck, oh fuck, make me cum, make my cunt fucking cum, fuck!"

Slick from fucking, hard from desire and frustration and disbelief, my cock slid deeper and deeper into Cally's ass. I'd never fucked anyone's ass before, the feeling was weird. . .tight, of course, dirty -- certainly!, very different from a pussy with its muscles and lubrication. I kept moving deeper and deeper into her ass.

"Oh God, mmmmmm, ooohhh, mmmmmm, Randall, oh mmmmmm," Cally threw her head back and moaned with unconcealed pleasure. "Mmmmmm, make me cum, baby, gimme all that cock. . .fuck me so fucking good. . ."

My cock was more than halfway in and my fingers were crooked in Cally's pussy around her G-spot. Her moans were coming in time to when my fingers hit a certain spot inside her. I made sure to run my fingers down that spot regularly. She nodded her head spasming and breathing hard. Meanwhile, my cock was beginning to fuck her ass, not just sliding inside her, but moving in and out now, deeper with every stroke.

"Can you fucking feel it, fuck, you can feel my cum fucking building. . .oh shit," Cally rasped out the words. "Just fucking don't stop. . .do it, fucking do IT!"

Now I was losing myself too. My fingers in her pussy and G-spot; my cock in her ass spreading it wide, beyond what it had ever felt. Suddenly my own balls tightened up with that telltale sign that I was going to cum.

"You're going to get an ass-full of cum, you whore, taking my cock in your asshole," I said. I had no idea where it was coming from but now there was no more talk.

Cally fucked my fingers and I fucked her ass. . .her orgasm arrived her and she yelled out -- a wild shriek of exalted satisfaction. She might have killed a mammoth, scalped an enemy, or defended her child. Her next whoop was into the bedspread and I could feel her gushing onto my fingers, a sacred geyser of her juices and her flavor. That downpour was the last straw for me and I felt my cock tense up and go balls deep into her ass. Then I came -- hard and long and what seemed like forever. Though I'd come less than 30 minutes before it seemed there was even more cum this time. As I came I imagined it filling Cally's ass and it made me buck and cum harder. Hot spurt after spurt.

We collapsed together onto the bed. Spent physically and coming out of an orgasmic trance. The only sound in that room was our breathing that was erratic, and harsh, and sometimes came in huge gulps that fed the worn out muscles we'd pushed to their limits.

As she lay there, I looked at Cally admiringly: the smooth curve of her ass, her muscled legs quivering a little after our exertions, the sweat running down her ribs, her hair wet and smelling of her oils and our fucking. I didn't like her, but I wanted her and realized how attractive she really was. Or how deprived I had been physically for a long time.

Casually I reached for my phone again: I looked at the time -- almost 4 in the morning -- then took another picture of Cally stretched out on my bed. I wanted to remember this moment.

She raised her head a bit, "We're good, right, Randall?" with eyes both confident and pleading.

"Yeah, of course."

"God, my ass is just. . .ow, God, I can't believe you fucked me with your huge cock." She was in pain yet still in the glow of the orgasm. I nodded in understanding.

"Can I. . .use your bathroom, to clean up, Randall?"

I nodded again. "Help yourself."

She pushed herself up off the bed slowly and in a lot of discomfort. Willing her legs over to the bathroom, she half-staggered, half-limped to the door and steadied herself there. Cally looked back for a moment, and said, "Those pictures are just for you, right?"

I nodded, "You kept your word and I'm keeping mine. A bet's a bet."

She smiled and closed the door behind her.



A Bet's A Bet



"It's time to wake up now."

With just those six words, I regained the ability to open my eyes. Regained? I guess that's not the right word. I'd only just dozed off—nothing more.

"Well, how do you feel?" The hypnotist grinned at me. I didn't see why he was grinning, though. He was a friend of mine. His name was Kyle and he liked to think he was a master when it came to hypnosis. I guess in a sense he was. I did get into a trance, after all—well, I did if that's what you call falling asleep from the weight of sheer boredom.

"No different, Ky. You suck at this." I really didn't feel any different. At that point I almost considered letting him call off the bet. You see, we had a bet going. He said he could turn me gay without making me less attracted to women—he thought he could make gay sex better than straight sex for me. I thought hypnosis was all bullshit, so I figured what the hell; it'd be an easy hundred dollars if nothing more.

"No different? Well, then, let's try this... faggot!" Right as he shouted that word, my right hand shot up in the air. I looked at it with what anybody who wasn't in my situation would consider a hilarious expression.

"What the hell!? How did you do that? Is that—am I stuck like this?" Kyle was clearly enjoying my expression of horror which lasted even after my hand was able to go down again.

"Don't worry, that trigger only works for my voice. Think of it as your way of telling me just what a faggot—"my hand shot up again"— you are. I hope you're ready to give me that hundred bucks." After that little show I considered begging him to let me off the bet right then and there, but a bet's a bet. They say hypnosis can't make you do anything you don't want to do so I managed to convince myself that I could still win it.

"Alright Ky, you made me raise my fuckin' hand. We'll see how you're feeling in a couple weeks when your wallet's a hundred bucks lighter." At that point it was time to head home. It was pretty late and I didn't want to get caught in traffic. I grabbed my jacket and was about to leave the house when Ky walked up to me holding a plain cardboard box.

"Here, take this box with you."

"What's in it?

"It's part of the hypnosis. Don't open it up until I tell you. "

"Alright, sure, whatever. A deal's a deal. I'll do whatever you ask until next week's up."

Box in hand I left his apartment and took the elevator to the first floor. It was raining outside but my car was in the parking garage next door. After I was safely inside it, I got curious about what he'd put in the box. I promised him I wouldn't open it—and I'm not the type to go back on his word—but I didn't say I wouldn't try to puzzle it out some other way. I gave it a shake, and there was a dull thud as whatever was inside of it moved around.

It was longer than it was wide, and made out of some kind of rubber. There were also a couple of other things in there. Some kind of can or something, and a smaller metal object. There might have been some other things in there but I couldn't think of any way of figuring it out without breaking my promise.

I sighed and set the box aside, then buckled in for a fairly uneventful drive home through the rain. When I got inside my house I checked my cell phone. I'd forgotten that I turned it on silent when I was being "hypnotized" by Kyle, so I turned the ring tone back on and set it aside.

After doing the usual house stuff—cleaning, cooking dinner, watching TV, and what-have-you—I decided to sit down and watch some porn. I got myself comfortable in bed and powered up my computer—it's set up right next to bed—and navigated to my favorite site, xhamster.com. It was only seconds before I started stroking my cock.

I'm reasonably proud of my dick. It's six-and-a-half inches—seven on a good day—with a little bit of a curve to the left. At the base I had thick pubic hair which I did little to trim or maintain. I kind of liked the way it made me look. Manly—powerful.

While watching yet another video of some silicone monstrosity taking dicks up her ass like a champ, I noticed something was wrong. I wasn't really relating to the man doing the pounding. In fact I was kind of fantasizing about what the girl was feeling. Believe me, when you're straight as an arrow that's a terrifying realization.

After a few minutes—long enough for my cock to fully deflate—I worked up the courage to test myself. I clicked over to some gay porn, picked at random, and waited for the video to load up. My heart was beating like shoes in a dryer at that point, but I calmed down a bit when the kissing and stripping didn't do anything to rouse my limp dick.

Needless to say I was pretty damn shocked at what happened when one of the men on the screen pulled the other's cock out and started sucking. My dick was standing at attention almost instantly and it was the hardest erection I've ever had. That was enough for me. I closed out the window and decided to go to sleep. It was an odd feeling, being sexually frustrated and yet disgusted with myself.

I checked my cell phone the next day, after work. Lo and behold, Ky had left me a message.

6:32PM Kyle Anderson: Hypno time. My place. Faggot!

My hand shot up in the air right as I read that—luckily the parking garage was deserted. It took me a few seconds to force my hand back down. And with that a night of masturbation and soul searching had been replaced with a night of hypnotism that I feared would worsen my decline. A bet's a bet, though. God damnit, I thought.

It was about seven thirty when I reached his apartment. Weirdly enough, I can't really remember what happened once I got in the door. I only really remember what happened after I got home that night.

My phone vibrated and the screen flashed with a message from Ky.

9:47 Kyle Anderson: Listen up queer, it's time for you to open the box. There's a note inside, it will tell you what you need to do.

I'd been damn curious about what was in the box. Finally it was my chance to figure out what was in there. Needless to say my curiosity died—or at least masculinity dictates that I say it did—when I opened it to find a flesh colored dildo—almost exactly the size of my own dick—as well as some lube, a can of womens' shaving cream with a pink razor, a rainbow colored cock ring and some panties. And the note...

Nick,

I'm glad you finally got to the stage of opening Pandora's box. Well, that's what I like to call it at least. If you opened this without me telling you to I'm going to be pretty goddamn pissed and you're going to be giving me my hundred bucks.

Anyways, it's time for you to start experiencing what it's like to be gay. I'm not going to touch your attraction to women; that's for you to figure out. I am going to give you a little taste of what you're missing though. Leave the dildo and the panties, those are for another time. I want you to shave your crotch. Balls, ass, everything. I don't want to see a hair anywhere down there.

You're also going to wear that cockring from now on. When you have everything groomed and the cockring on, I want you to take a picture of yourself bent over with your ass cheeks spread. Then you're going to jack off.

-Kyle

When I first read the note, I was incredulous. Did he actually think he was going to make me do that stuff? It was only after my body started moving to carry out the actions prescribed that I got worried. I watched, detached, as I looked up a guide for how to shave my pubes and, after trimming myself as closely as I dared, slathered the sweet-smelling shaving cream on my unmentionables and slowly but surely shaved all the hair away.

When I was done, my crotch was as smooth as the day I was born and the cool, tingly sensation of the shaving cream was almost arousing. I automatically put the cockring on and went into my bedroom. I bent over on my bed in front of my computer, and used the webcam to take several pictures of myself with my ass cheeks spread.

After emailing them to Kyle, I jacked myself off. The ring made my cock bigger than it had ever been before, and thick veins bulged outwards in places where my cock was once smooth. I came in less than two minutes, and sprayed cum all over my chest. Believe me, that was not a fun mess to clean up. After I was done and the post-masturbatory haze had washed over me I was taken by a sense of anger. The game had gone far enough. I'd give Kyle his money but I wasn't going to risk being turned into some kind of gay fucktoy robot. That was when I saw the email alert flashing on the screen.

After reading what it said I was almost in a state of shock. Kyle said if I didn't keep going with the hypnosis until the end of the bet he'd send my pictures to everyone I knew. I was stupid enough to include my face in one of them, so I knew I was pretty fucked. He did say that right after the bet was over he'd let me watch him delete them. I suppose the only consolation I could give my past self if I were there is that eventually I would come to love the fucking.

The next couple hypnosis sessions passed with few notable events. Aside from making me keep up on the grooming of my pubic hair, Kyle didn't tell me what he was doing to me while I was under. He did forbid me from watching porn though. I'd agreed to his terms at the beginning of the bet, and I didn't want to get humiliated in front of my friends and family, so I did as he asked and avoided porn like the plague.

By the third day my bare cock was aching in its desire for pleasure. The problem was whenever my hormone-flushed brain tried to think of some fantasy, I couldn't think of much other than gay sex. The gay thoughts did help with my erections though. Whenever I thought of something gay my cock lost any semblance of hardness. I was having some problems with precum though; there were times during those few days where I would go to the bathroom and pull down my pants only to find my ringed cock and balls slick and sticky.

It was on the fourth day that I received an email from Kyle outside of our normal, hypnotic meetings which I still have trouble remembering.

Hey Nick

It's time for you to take it to the next level. I'm sure you know by now that manly men have hair on their balls and assholes, because they don't need to be pretty down there to please their lovers. You can't have hair on your asshole though. Around men you only care about their cocks, and why would a cock go into your asshole if it's not pretty? If you wanted to put your dick in something you would find a woman, but you need something hard and thick in your own tight little hole, and there aren't many girls with a clit that big. That's why you wear the rainbow cockring; to make your dick look cute for all the guys. It's not like they want it to look manly or strong. They want to see a cute little cock and balls swaying back and forth while they hump you. In fact it makes you uncomfortable when you're naked around a man and he sees that your dick is bigger than his. That's why you can't get hard whenever you're looking at a man. You want him to focus on fucking your ass, not your cock. In fact, when you see a man naked your dick goes limp, no matter how hard it was before, and you get a burning feeling in your ass. The only way to relieve it is to put something in there. If you rub that special spot in there enough, your dick might get just hard enough to let out a stream of precum. It'll feel amazing, but you're not going to be fucking any men with that cock, no matter how they might beg you to. Your cock is for women. Your ass is for men. From now on I want you to wear panties, the first pair is in your box. I'll give you a new pair to wear every time you come for a hypnosis session. I want you to try to masturbate to gay porn tonight, but you can't touch your ass.

-Kyle

I almost thought it was funny the way he was trying to convince me that his hypnosis was having the effect he wanted it to have on me. If he wanted me to be attracted to men, my dick would be getting hard when I saw them. I figured I'd humor him—see if I felt any attraction to men at all. After putting on the panties, I loaded up xhamster and picked a video. I made sure it was one about the largest, most powerful looking cock I could find going into someone's ass.

At first the video had no effect, as I watched the larger man overpower and tie the smaller one up. It was when the large man pulled his penis out, ten glorious inches nested in a bed of dark curly pubic hairs, that I began paying rapt attention. The younger man who was tied in a very compromising position, barely more than a boy to be honest, paid some token pleas for mercy. His soft cock dangled above his own mouth. The pleas came to an end as the large man slowly slid his thick member into the younger's ass.

At that point I pulled aside the panties and tried to get myself to harden. No matter how harshly or gently I rubbed, though, I couldn't get myself hard. It felt good, but I knew it wasn't going to help me cum. To be honest, I looked more like a woman rubbing her clit than a man masturbating to porn. My own ass had a burning feeling in it, and I was desperate for relief, but I couldn't bring myself to touch it. Several minutes of thrusting and moaning followed, before the most spectacular thing that I've ever seen in porn occurred.

The young man's cock—which had slowly hardened throughout the film—began dripping cum onto his face and into his mouth. The large man kept fucking him as cum slowly poured out of his dick. His moaning had turned to frantic screaming of pleasure at that point. As the waterfall waned to a slow drip, the large man pulled his dick from his fucktoy's ass and stroked himself a few times. He sprayed his semen all over the young man's ass and balls, and then went to his knees and forced the young man to lick his softening cock clean of any remaining cum.

It was at about that point that the video ended, and I was left in the terrible state of being incredibly aroused and yet unable to get hard. My ass was burning, practically screaming at me to put something inside of it, but I couldn't move a muscle to touch it. It took me a couple hours to calm down enough to get some sleep.

I slept in until eleven—thank god for national holidays—and was woken by a phone call. I looked at my cell; it was Kyle.

"How are you feeling? Sleep well?" That cocky, sarcastic voice... I used to like it.

"How well do you think I slept? What are you doing to me?" The words sounded indignant, but my heart wasn't really in it. I was tired of fighting him and—I truly hated to say it—I was beginning to enjoy the feelings he was causing.

"I'm only doing what I said I'd do. I'm turning you gay. Do you think you can hold out for five more days, Nick?" Truth be told, I'd started doubting that I would win the bet at about the time when he had my body moving against my will.

"We'll see, Ky." It was hard to even be confrontational with him. His voice had already changed me so much.

"Yeah, I guess we will see. Faggot!" He hung up on me right as my hand shot up in the air. If I weren't so sexually frustrated I would have probably done something stupid. As it stood I went about my day until about two o'clock, when he sent me a text message.

2:07 Kyle Anderson: Alright Nick, big day with the hypnosis planned. Get to my place by 3... and bring the dildo.

Redness shot to my face as I remembered the dildo, flesh colored and veiny, which I'd almost completely forgotten about. I wasn't quite sure what he wanted to make me do with it, but I had my suspicions by that point. I grabbed the cardboard box which contained the dildo, and hopped in my car. It took me about forty five minutes to reach Kyle's apartment complex, so I was hurrying a bit after I found a parking space in the garage. When I stopped for a moment to think, I couldn't figure out why I was hurrying to meet the destruction of my sexuality.

As usual I have no memory of several hours after I got in the door of Kyle's house, but I will tell you that my asshole felt sore afterwards, even though the sexual frustration still remained. However, when I got home that night something amazing happened. I was frustrated yet resigned to a fifth day without cumming when I got a call on my phone. It was Kyle, and if he were with me when he said those words I would have sucked his dick on the spot. He wasn't, though, so that came later.

"So Nick, you're going to do a few things for me, but afterwards I'm going to give you a reward." I was intrigued. Frankly I had no clue what the reward could be.

"What am I going to do for you, Kyle?"

"You're going to shave yourself. All the body hair, gone. I don't want anything below your eyebrows. Then you're going to get your webcam, set it to record, and fuck yourself for me. I loosened you up today while I had you under, but I made sure not to let you cum."

"Yes master," I said before catching myself. Master? What the fu—but at that point my body had already begun its automated tasks. An hour later, I felt like I had been reborn. A fully shaved body is a beautiful thing. My skin felt soft, and the air washing over it gave me goosebumps. Simple, everyday things like the rub of my jeans against my panty-clad—although he had been moving me more towards thongs recently—ass were new sources of arousal.

Anyways, enough about the simple pleasures of a smooth body. After I was finished admiring my handiwork in the mirror, I set myself up comfortably on my bed. I was propped up, with my lower back against some pillows and my legs spread wide, giving full view of my asshole and cock. The thong barely covered my balls, in fact they hung out to either side. My asshole was clearly visible, with only the thin string of the thong covering a small part of it.

The feeling of the thong in between your butt cheeks, rubbing your asshole whenever you take a step can only be described as divine... but also incredibly, frustratingly arousing as I would later learn. But that was a problem for a different time.

I lifted the dildo with great reverence, and as I did the ever-present burning sensation in my asshole intensified. While I coated it in lube, I grinned inwardly—I finally had a way to relieve myself. Fantasy upon fantasy swarmed my mind as I pulled my thong aside and the dildo easily entered my asshole. When I felt the rubber balls slap against my butt, I held it there for a while. With the dildo stretching my insides, I tensed and relaxed my ass, reveling in the sensations. After a minute or so, however, that was no longer enough. I had to fuck myself. Slowly at first, and then with greater speed I slammed the dildo into my asshole. Eventually I was fucking myself so hard my hairless balls were bouncing up and down and my soft cock was swinging back and forth.

The orgasm—if that's what that amazing, transcendent feeling could be called—came upon me in waves, and without notice. I didn't even realize I was screaming until the climax had passed. Afterward, I laid there for several minutes enjoying the afterglow; my semen had drenched my balls and fallen to coat the base of the dildo that was still impaling my sore asshole.. I reached over to my computer and sent the video to Kyle. I removed the dildo from my ass and put it back in its box, then laid down in bed still covered with my own cum. It wasn't long before I fell asleep. I'm sure you can imagine how uncomfortable it would be to be woken up in such a position.

...Which is exactly what happened, as I opened my eyes to see Kyle's own. He grinned that cocky grin of his and told me to get up and take a shower. I automatically did as he commanded, and it wasn't long before I found myself standing naked in front of him, bare body on display, with only my thong and the rainbow cockring for adornment.




A Bet's A Bet



"So, Nick, I think I've won the bet right?" At that point I'd be lying if I said he still had a ways to go.

"Yes, you won." I found my wallet and pulled out a hundred dollar bill. "Here's the money I owe you." The old me would have tried to weasel out of it somehow, but I couldn't fathom trying to trick Kyle.

"Thank you, Nick. I can think of a way for you to earn it back, though." I thought I knew just what he had in mind. I licked my lips.

"And how would you have me do that?"

He unzipped his jeans and pulled out his already hard dick, which protruded from a thick nest of pubic hair—six inches, the old me would have been proud to know his dick was bigger. But I'm not the old me, and I'm glad that I can't get hard anymore around men because then my cock would have been visibly bigger than his, and that would be very wrong. In fact, just the thought of my cock being bigger than his was enough to keep me soft.

"Suck it, Nick." I instantly went to my knees in front of him, and took him into my mouth. I was surprised at how easily I did it, to be honest. I'd never tried deepthroating before, and unless he had been doing a lot more than I knew, just the hypnosis was enough to rid me of any semblance of a troublesome gag reflex.

The slurping went on for several minutes before he made me stop. By that point the burning in my ass had grown almost unbearable. "Let's go somewhere more comfortable, why don't we?" He led me to my couch, where he sat and spread his legs to give me easy access to his dick.

"Get back to it," he said and I instantly resumed sucking his dick. Occasionally I'd pause to toy with the sensitive area under his head, or I would try to hold his dick inside my throat as long as possible, and swallow around him hoping the squeezing would feel good on his cock. That brought tears to my eyes, but I didn't care. I just wanted his cum. It took several more minutes before he shot down my throat. Imagine my surprise when I felt a steady stream of cum dripping from my own cock, soaking through the thong and pooling on the floor between my knees. After a few moments of basking in the pleasure of it all, I looked up at him with a questioning look.

"Figured that the perfect bottom needs to enjoy more than just getting fucked." He was clearly enjoying it almost as much as I was. As amazing as my orgasm had been, it was just that: an orgasm. I could have gotten that from fucking a girl. That did nothing for the burning in my asshole, the aching need for something to fill the space. After I spent a minute or so cleaning what little sperm escaped my mouth off of his cock, I felt him shove a couple of twenties into the waistband of my thong.

"Buuut... it's time for the main course. I'm going to fuck you right here." He made me turn around and sit on his lap. Before I sat down, he reached around and pulled my thong to the side so that my cock and balls could flop out. I sat slowly, wanting to enjoy every second of the first cock my heretofore virgin ass had received. When I finally felt my smooth balls resting on his rough, hairy sac, I was in heaven. He put his hands under my legs and made me bounce on his dick for a long time. Since he'd just cum it was going to be a while until he was ready to do so again, and I was prepared to enjoy every moment of it.

By the time he was bored of my bouncing, my legs were very tired. When he told me to get up and move to the bed, I did so shakily, and when he told me to bend over and go down on my hands and knees I did so gratefully. He fucked me, hard and deep, for several minutes. When his dick was pushing in, I relaxed my asshole completely. When he pulled out, I tightened on him, trying to make it as pleasurable for him as possible. My prostate was taking a beating and every once in a while some watery cum would shoot from my dick, accompanied by a wave of pleasure.

"Stop, Nick... I want you to look at me. Get on your back." I was drunk on sexual energy at that point, and I quickly positioned myself on my back, propped up by pillows and with my ass hanging off the bed. He looked at me for a moment, my legs spread and bent at the knee, body hairless, cock limp and ringed, and then bent towards me. The top side of his rock hard dick pressed between my butt cheeks as he kissed me.

"I hope you're enjoying this as much as I am," he said as he pulled away to catch his breath. Whenever our lips touched it was like electricity coursing through my body. He kissed me again, more deeply, and our tongues rolled over each other in a carnal ballet. He pulled away and looked me in the eyes. "You know, I've always loved you... and I knew you were gay all along." A small part of the old me was horrified by that, and I pulled him in for another kiss to stop him from continuing. He obliged for a moment, but then pulled away again. "Hypnosis can't make you do anything you don't want to do. You wanted this."

Woah. That was a shocker, let me tell you. I was Nick, straight as an arrow, manly as hell, great cock and what-have-you, completely shaven and lying on my back with my legs curled around another man whose cock was pressing hard against my asshole, with my own dick lying limp. I stared at him for almost two minutes. That's when he did the last thing I expected. "I'm giving you back your free will. It's your choice now."

It took me a moment to think. He'd shown me pleasure unimaginable, taken my free will, turned me into his own personal fucktoy... but then he gave me my freedom back. With that in mind, I knew what I had to do next. "Alright Ky, I've made my choice." I paused, then reached for his dick. "Fuck me." I guided him into my asshole, and at that point he knew what to do next.

We made slow, sensual love. When he finally came inside my ass, he set off a climax that had been building for what seemed like a liftetime. I felt all the pleasure in the world course through my body as spurt after spurt of sperm left my soft cock. By the time I was done, his own dick rested limp inside my asshole and our bellies were coated in sperm. We fell asleep like that, together.

TELL ME WHAT YOU THINK. :D



A Bet's a Bet



I take my daughter to a dance class each week. Her teacher is Nicky and I have to admit I have always had a thing for her although as a married man I never intended on acting on my desires. What is more I always thought the fit and bubbly dance instructor was way out of my league.

Standing about 5 foot 6 inches tall and weighing around 110 pounds, Nicky is 30-years-old. She has long, brown hair that is rarely not tied back in a ponytail while one of her most outstanding features is her dazzling bright blue eyes.

Full of energy and enthusiasm as befits her job, she has an athletic but not overly muscular build and a liking for wearing figure hugging clothes. Often when attending my daughter's shows I have to concede my glance does linger on Nicky's shapely form sometimes a lot more than what is happening on stage.

One evening after I had returned home with my daughter after her dance class I realised we had left her sweater behind. She too had noticed and, as it was her favourite, she begged me to return to the dance studio and get it.

The studio was only a mile or so away and I'm a soft touch for my daughter so I agreed. Leaving my daughter to get ready for bed under her mother's supervision I drove the short distance to the studio.

As I looked through the glass in the door leading to the studio I saw Nicky going through a series of stretches. I watched transfixed as she contorted her beautiful body into various positions and as I did so my dick began to twitch and harden.

Snapping myself out of it but still unable to avert my gaze, I reached for the door handle, turned it and silently crept into the studio not wanting to disturb Nicky.

Her back was to the entrance and she continued her limbering routine as I quickly and quietly made my way across the room. She bent over to touch her toes and held the position as I arrived within feet of her. "Hi there. Enjoying the show?" she said.

Her sudden remark startled me. "No...I mean yes...I mean no," I mumbled. "Sorry. I didn't mean to interrupt," I said regaining some of my composure. "My daughter left her sweater behind."

Nicky stood up and faced me. Grinning she said, "Oh ok. Is it that one?" She pointed towards a bench where the sweater was neatly sitting.

"Yes that's it. I will get it and leave you to finish your workout in peace."

She replied, "Stay if you like. I enjoy an audience." She giggled and resumed her stretching.

"Was she flirting with me?" I wondered. "Surely not." My dick twitched in my shorts again. I picked up the sweater and made for the door.

"I've seen you looking at me before you know," Nicky said stopping me in my tracks. I mumbled an inaudible protest at that suggestion. "It's ok. I really don't mind," she said. "Do you like games?" she asked.

Without thinking I nodded as she walked towards me. Standing only a foot or so away with sweat dripping off her golden brown skin she smiled seductively and said, "Me too. How about we play one right now?"

Again I nodded not knowing what to say and what would come next. "Great," she said with a beaming smile. "You know the dance school is always short of money for equipment?" she enquired. I nodded. "Well what we will do is play a game and each time I win you donate 50 dollars to the equipment fund."

Intrigued I said, "And if I win?"

She giggled once more. "Each time you win I'll take of an item of clothing sound fair?"

My dick twitched yet again and, amazed by this proposition, I said: "Yes." She giggled and skipped off to fetch something from her kit bag returning with a pack of cards. 

We both sat on a bench and she shuffled the deck. "Single highest card wins game ok? I'm not into slow games that you have to think about," she said with a grin.

Still transfixed I nodded my agreement and she turned the deck of cards over between us. "You draw first," she said.

I drew a two and she let out a laugh. "Typical," I thought cursing my luck.

She drew a five and said, "That'll be 50 dollars please." Shaking my head in disappointment I reached into my back pocket and handed over the bill from my wallet.

"I'm not wearing much clothing you realise," Nicky said coyly. I gulped and reached for the cards. This time I picked up a 10.

"That's more like it," I thought. She drew a three and tutted at her misfortune. It was now my turn to grin as Nicky stood up and quickly peeled off her bright yellow t-shirt to reveal a dark blue sports bra.

She sat back down and I picked up another card from the deck. A king. Sighing she drew a five and swung her legs round to remove her training shoes.

Neither of us spoke as I drew a jack. She followed with a nine. "So close," I said in fake sympathy. Nicky curled up her nose half grinning and stood up.

She turned her back to me and moved her hands to the waistband of her black leggings. Turning slightly so she could see my reaction she tucked her thumbs into each side of the waistband and began to slip the clothing down.

She lowered the leggings to her feet revealing her bronzed and amazingly toned legs as she did. But what was more their absence revealed the golden rounded mounds of her perfect bubble butt which were separated by a tiny dark blue thong. I gasped. I'd often fantasised about her perky butt but now it was right there.

Casually Nicky stepped out of the leggings and threw them onto the bench. She sat down facing me again and I drew a king from the deck. "Come on," she exclaimed in mock frustration as she picked up a two.

To my disappointment Nicky swung her legs round and took off her little white socks. Giggling she said, "They're clothing too you know?"

Attempting to hide my disappointment I nodded and picked up my next card which was a six. She drew a nine and, eager to get on with the game, I handed her another 50. My hand was shaking as I gave Nicky the bill and she smiled sweetly and calmly said, "Thanks."

Next I drew a seven and to my glee she only got a four. "Yes," I yelped. Without replying she stood and reached behind her back to unhook her bra.

It made a quiet pinging sound as the clasp released and then Nicky slipped her arms out of the straps dropping the bra to the floor between us. Briefly her hands paused cupping her breasts before she took them away giving me my first glimpse of her tits. I'm no expert but I'd say her glorious globes were 34c and she obviously sunbathed topless as their colour matched the beautiful bronze tone of the rest of her body.

"Like what you see?" she asked. Again all I could do was nod.

Nicky sat back down on the bench again. Briefly taking my eyes from staring at her bare boobs I picked up a seven from the pack of cards. Looking straight at me her hand moved towards the deck and paused for a moment. "I hope it's a good one," she said as she turned the card over. It was a four!

Delighted but this time controlling my words I said, "bad luck."

"Yeah right," Nicky replied with a chuckle as she stood up once more. Turning away from me as she done had earlier she reached either side of her thong and started to slip it down her butt.

I watched as her tight butt hole appeared followed by her pussy lips. She slipped the clothing ever so slowly down her athletic legs stepping out of the tiny piece of material as it reached the floor. She bent down to pick it up and as she did so her pussy lips parted slightly. My dick twitched again.

"That's it then. Game over," she said her words snapping me out of my admiring trance. Dropping the thong onto the top of the pile of her crumpled clothes she turned to face me giving me my first look at her shaven pussy from the front. I gasped with excitement and Nicky grinned.

"Want to play on?" she asked.

Curious I replied: "What are the stakes? You're out of clothes."

Smiling she said, "If you win the next hand I will let you touch me."

I gulped and muttered, "Ok but touch you where?"

"Anywhere and anyhow you want," came the response which was just what I had hoped for.

Quickly I picked up the next card. It was an ace. She drew a queen. Not knowing what rules we were playing to I asked, "Are aces high or low?"

"High," she replied and I almost leapt off the bench. Laughing at my obvious eagerness to claim my prize Nicky said, "It seems I'm all yours. Where do you want to start?"

Gasping and still not sure if this was really happening and, if it was, not certain she had meant what she said I paused. "Can you turn around please?" I asked.

Nicky chuckled, "You're the boss and since you asked so politely of course I can." She stood up and turned at which point I moved in.

I rubbed both my hands all over her butt culminating with gliding one finger over her butt hole and then her pussy. To my surprise and pleasure her pussy lips were slightly wet. My anxious dick twitched again.

"Enjoying yourself back there?" Nicky enquired. I did not answer and instead placed my finger at the entrance to her pussy.

"Can I?" I asked hopefully.

"No problem. You won fair and square," came the reply. With that I pushed my trembling digit into Nicky's ever mostioning pussy.

Her pussy felt warm and inviting. She bent forwards placing her hands on her knees and arching her back to allow my finger easier access to her mound.

I was just losing myself in the glorious moment when Nicky broke the silence again. "You want to put something else in there?" she asked.

Unsure if I had heard correctly I shyly replied, "What?"

Slightly puzzled sounding she said: "Your dick. Do you want to put your dick inside me?"

With all doubt gone in an instant I simply said, "yes."

Quickly I pulled off my shorts and underwear. My dick was fully erect and pre-cum was dripping from the tip. With my hands I straightened her body up slightly. At the same time I put one of my feet between hers and kicked them apart.

Then after quickly rubbing my rock hard dick on the smooth, silky, golden brown skin of Nicky's firm butt cheeks I slipped it into her pussy.

She let out a gasp as the tip touched her pussy lips and then the shaft began to enter her hole.

Nicky's pussy felt warm and wet as I slid my dick further and further in until the whole shaft had disappeared into her. My balls touched her skin as the entire extent of my hard dick made it inside her pussy. I stopped moving and paused to enjoy the feeling. It was better than I had imagined and I wanted to fully appreciate the wet, warm sensation.

Just as I was taking in the moment I was shocked as I felt Nicky's hips move back and her pussy muscles flinch.

"Go on then. What are you waiting for? If you're going to fuck me then fuck me," she said.

Surprised but delighted by her apparent willingness to 'seal the deal' I began to thrust.

Slowly at first then picking up pace I thrust my dick in and out of Nicky's ever mostioning pussy.

To my glee she began to softly moan with pleasure and I picked up the pace. The sound of her juices was now audible and I pounded harder and faster. Then suddenly her pussy muscles contracted and squeezed tightly around my shaft as she orgasmed.

Pussy juice flowed over my dick and out of her lips dripping onto the floor. I was thrilled that I had made her orgasm and I was not far off cumming myself but there was one last thing I wanted first.

I slid my dick out of her soaked pussy as Nicky continued to moan in post-orgasm pleasure. My dick twitched as if to protest at its removal from her pussy. I put my hand on the small of the dance teacher's back and pushed her gently down a bit. Then I positioned my dick at her butt hole and pushed its tip inside.

Seemingly over her orgasm and for the first time apparently reluctant to let me do as I wanted Nicky said "no."

Disappointed, I was about to pull out when Nicky spoke again, "Sorry. A bet's a bet. I set to rules of our game and you won. Go on. Do it."

Not needing a second invitation I pushed the tip of my dick deeper into Nicky's butt hole and slipped my shaft, still soaked in her juices, down into her anus.

Again I paused to take in the feeling. It was even tighter and warmer than her pussy had been and my dick twitched one final time. I thrust my hips forwards and pumped my dick in and out of her ass hole. Giving herself totally to me Nicky groaned as I pounded her butt.

I could feel the cum making its way up my shaft and I thrust quicker until it was time. With one last thrust I plunged my dick into her as far as it would go and as my balls smacked against her butt cheeks I came.

Cum spurted out of my dick like never before. It fired out and kept cumming. I yelped in ecstasy as my creamy cum shot into her ass filling it with my juices.

Nicky squealed loudly, "You fucking came in my ass!" Her reprimand startled me but just as I was about to apologise she sighed playfully and said, "You certainly collect on your bets."

I pulled my dick out of her and as it left, my thick, white cum started dripping out of her now gapped but still tight looking anus. Some of my cum joined her juices in a growing puddle on the floor while some trickled down her butt cheeks and onto her legs.

Still admiring the sight in front of me I pulled up my underwear and shorts. Standing up and heading towards her kit bag Nicky smiled at me and said: "Thanks for the game."

This time it was my turn to chuckle as I replied, "My pleasure." She pulled a towel from her bag and began wiping off her pussy, butt and legs.

Regaining my composure I said, "See you when I drop my daughter off for class next week."

I made for the door when Nicky called me back. "Aren't you forgetting something?"

Turning around I saw her, still naked, holding my daughter's sweater.

"Oh yes," I replied. "I got distracted and forgot."

She chuckled and handed it to me. "Bye then," she said with a smile.

"See you next week," I responded with an even bigger grin and with that I headed off from the studio.