The IT Guy Pt. 04

"I still don't understand the bracelet, he buys it for you and tells you you can keep it if you don't fuck him?" James said holding her wrist looking at the expensive piece of jewelry, "If he wanted to make me jealous by buying you something we cannot afford, it is working...I was going to say give it back, but you agreed to give it back only if you guys fuck. Crap, I hate this thing."

Anne looked at James, "I've thought a lot about this since at first it made no sense, but there's a possibility it was just a joke and there's no meaning to it, but..." Anne hesitated.

"But, everything Davenport does is with a purpose, you wanted to say." James sighed.

"Ok, let's look at this from his angle. First of all every time I look at it, I am reminded of the possibility, the promise of sleeping with him, plus every time you look at it, you have to be thinking the same thing. What if I shower and forget to put it back on and you come home from work...I wish I hadn't said I'd leave it on until...."

"Fuck him. Let's just take it off and throw it in the jewelry box, or give it back to him and tell him to give it to another of his willing women." James spat.

"No, I also like teasing you wearing this, and perhaps I'll intentionally leave it off some day. I know how excited you get thinking how close I came to...anyhow, I see other motivations for John. Let's say he bought me a $5,500 bracelet and I sleep with him because I am so grateful. That just makes me a whore and second, he wins me over not by this wit, charm and large dick, but by buying me. He doesn't want that, he wants me to come to him and let him take me willingly." Anne finished. "Also, he wants you to know he's had me, you see I no longer have the bracelet and I don't need to say a word, forget about Schrödinger."

"Why would a bracelet prove you came to him willingly...never mind. Crap, this raises the level of willingness, or rather eagerness. You want him so bad you'll be sacrificing this bracelet just to have sex with him. That would represent a huge victory for him, you open your legs and in effect you pay him $5,500 for him to take you." James said bitterly, "God, he's good, no way this was a joke. What about the cocktail dress, where is it? I want to see it on you."

Anne got up, "Stay here, I'll go get it."

Five minutes later Anne came back into the bedroom wearing...almost nothing, or at least that is what James saw. Anne twirled in a skin tight, thin satin or silk dress so short that it that barely covered her ass and pussy, her back totally exposed down to just above the crack of her ass, but the side panels were what drew James' attention. They were 6 inch wide sheer strips of fabric that went from her thighs to her armpits. "Anne! I can see your boobs from the side, and how will you wear a thong or panties? How the hell will you sit down?" James sputtered.

"I know, I am not sure if I can wear this out in public, but," reaching behind her she pulled on a matching light jacket, "this goes over it, so I can walk around without being totally leered at."

"Sit down, I want to see how exposed you are. No way can you go out with Davenport wearing that, no way."

Anne walked over to the chair in the bedroom, taking off the jacket she pulled down the hem and with great care sat in the chair with her legs tightly closed. "See, you can't see anything."

James looked at her, "Relax and let your legs just open naturally, yeah. See? I can see your slit right there."

"Maybe I should take it back, it is really revealing." Anne said sadly.

"Anne, I know you want to wear this, but how about this? You drape the jacket across your thighs when you are in the car and put your napkin on your lap at the restaurant. Nothing much we can do about the side-boob issue, but, damn! You look really hot in that. Come over here." James said.

James stood up and kissing her, put his arms around her, letting his hands roam down to her ass cheeks peeking out from beneath the hem. Anne's tongue was eagerly probing his mouth and he could feel her pubic bone grinding against his stiff cock. He slid his hand between them and found a slippery wet slit welcoming his finger inside.

"Oooooohhhhh, yessss. I want you to lick my pussy, lick my pussy with me in this dress." Feeling James' finger attack her pussy harder, she moaned, "Yes, you like that don't you, you like thinking about John's tongue right there, he'll surely want to do that seeing me in this dress..." She pushed James to his knees and opened her stance allowing James to press his face into her moist cunt. "Oh God yes!! There, there....fuck me with your tongue. Yes, that's it, deeper..." Anne moaned feeling James' finger push into her ass.

James started roughly finger-fucking her asshole while driving his tongue deep into Anne's wet hole, pulling her onto his tongue with his finger in her ass. His lips were getting bruised with her thrusting pelvis and was rewarded when she started panting rapidly and bucking harder against face. James had to swallow all the flowing juices and when she was done, he slipped his finger out of her ass and let her flop back on the bed. He stood up looking down and her drenched pussy exposed with her legs splayed wide and pulled his pants off.

"Wait," She said, "I want you to do me from behind as if you are just seeing me in this dress for the first time." Anne got up and stood in front of the dresser, pulling the hem down as far as she could. She felt James' cock first poke her, then press his dick against her ass.

He wrapped his arms around her, "I saw you standing here alone, where is your husband? Why would he leave you alone?" He said feeling the warm sides of her breasts through the sheer fabric before reaching around and cupping her breasts.

Anne rubbed her ass against his throbbing cock, "I think he is off tit-fucking some busty babe, or perhaps burying his cock in her ass, since he doesn't get that from me, you know how it is, boys will be boys. You planning on doing anything with that, or just hump my ass?" Anne purred as she bent over onto the dresser.

James felt her dress pull up as she bent over and her bare skin on his balls. "My wife won't let me fuck her ass either, where is this busty babe?" James said looking around, "Think he'll let me have a go when he's done?" He grabbed his dick and started sliding the head up and down her slit feeling the lips part.

"You really want to take me like that? I said he can't have my ass, I never said you couldn't." Anne bent forward pressing her chest onto the dresser, and when James pressed his cockhead against her anus, she pushed back letting out a moan as the cock readily slid in. "Yes, that's it, fuck my ass."

"I love your dress, I didn't even have to pull the back up to get at your ass, all the men here are going to love this, plus I love your shaved pussy when your juices flow. Your husband has no idea what he's missing." James said while rapidly rubbing her clit.

Anne was getting close to cumming and thrust back against James' finger and cock, "Crap, you feel good, why didn't I do this with the pool boy...ahhhhh, or the mail maaaaannnnn. Uh, God yes, there. We wouldn't have all these little bastards running around, Oh God, I'mmmm cummmmminnnnng." Anne slumped onto the dresser panting.

James grabbed her ass and started pounding her faster until he began to feel his balls ache and with a long moan filled Anne's ass with his hot cum. Slumping down on top of her he panted, "Ok, we're keeping the dress."

Anne groaned, "Why do I let you punish my ass like that? Let's get cleaned up and see if this thing is dry clean only." She said while peeling off the slinky dress.

"Ok, tell me about the Bahamas." Anne said as they settled on the couch in the living room.

"Yeah, ok. I was really nervous when we got on the plane and it wasn't made any easier when Lexi pointed out there was a clothing-optional beach down from where we were staying." James said, "And it didn't make my stomach feel any better with the thought of being naked with her and my assumption the Davenport would be calling you... ten minutes? He waited that long?" He added bitterly, before relating the trip to the Caribbean.

Lexi spent the entire flight leaning over to James making a point to press her sizeable breasts into his arm. She kept saying how exciting it was for them to be working so closely together and she knew they'd be even closer when the trip was over.

James tried to push the thought of Lexi and him out of his mind while also trying not to think about Anne and Davenport. "Lexi, I'm going to close my eyes for a bit since I need to catch up on sleep."

Lexi giggled, "I'll bet. You and Anne kept each other up to make up for the coming dry spell? But you seem bothered by something, don't you want to be with me on this trip?" She finished pouting at him.

"No, no, I like being with you. I'm just thinking about other things, don't worry about it."

"I know what's bugging you. You're thinking that John is going to be hitting on your wife while we are away. You're bothered that she'll like it." Lexi said seriously, "Actually, I know he will be. He told me that he welcomes the challenge, but your wife seems tough. Relax, you know that you can't do anything, so just enjoy the moment."

"He told you? You talked about Anne? Why would you guys discuss her and his...whatever, I'm going to sleep." James said angrily sliding the pillow behind his head.

"We talked about you too. He mentioned he saw how you looked at me and that I'd better watch out. It wasn't just about your poor little wife." Lexi said with a huff.

A while later James turned to Lexi, "I'm sorry, I shouldn't have snapped at you. I know you and Davenport are friends, strange friends, but what the heck. Let's just talk about the project. I think we can get through the hardware set up by the end of the day Tuesday. Then do the software installation and run some stress tests starting Wednesday."

Lexi turned to James, "I'm sorry too, I should realize that it has to bother you having John alone with Anne. She's a grown woman and not some innocent high school girl, unless John asks her to dress like one, he likes that." Lexi giggled, "Sorry, sorry, it was just a joke." She said laughing when James glared at her. "Come on, you've been apart before, haven't you?"

"Actually, no. You know we got married in January and I've not travelled anywhere, except on our honeymoon. And neither has she."

"I guess that's right," Lexi said, "I hadn't thought about that. Well, this will make future trips easier, unless...never mind."

"Yeah, unless. Can I trust her for future trips? On the other hand, perhaps I'll never know." James said quietly.

"Why wouldn't you know, you think she'd cheat on you and not tell you? I guess you know her better than I do."

James closed his eyes and tried to block out any images of Davenport and Anne, but that proved impossible so he faked sleeping the rest of the way.

The first few days were a lot of work at the bank followed by dinner meetings after which they both came back to their rooms with the incredible views of the ocean and flopped down and did very little other than sleep. Finally Thursday they were able got away and go find a meal on their own.

James looked over at Lexi after finishing a great meal with the sun showing off her great figure from the side. "You were really good this week, we got through the hardware and software installs without a hitch and all the testing went perfectly. Makes me nervous though, nothing should ever be that easy."

"I'm that easy," Lexi laughed, "though you won't even try? Will you? But, thanks, I was surprised how easy it all went, I think the president expected a lot of delays. Want another umbrella drink?"

"I do, but I'll pass since I hate to think how my head will feel in the morning as it is, but these really go down easy...Yes, I know, so do you." James laughed seeing Lexi start to speak. You just like teasing me, or do like sex a lot? Never mind, none of my business."

"I like sex a lot? I've seen you look down my top, you are fixated on my breasts and I know you'd like to see them, so I might tease you and flirt with you, but at least I'm honest. Tell me you haven't thought about your cock nestled between them."

James got really red, "I'm sorry, I try not to look, but your tops are so loose and...ok, yes, I would love to see them. What guy wouldn't, unless he's like the concierge, but even though I'd love to, I can't. I can't do that and live with myself knowing I'd cheated on Anne. But, be honest with me, if I were single, you'd most likely not even flirt with me, you like the tease. You like the challenge of getting a married guy on top of you." James responded.

Lexi looked thoughtful while scanning James' face, chest and arms, "I am not so sure about that. I agree, I love it when married men let go and go at me like they've never had sex in their lives, but you are different. You've got brains, and you're nerdy. Did you know everyone around calls you the IT Guy, even other people in IT? You focus on your scripts and tools and pay almost no attention to anything else, but you get aroused as quickly as I've ever seen," Lexi giggled looking down at the table, "but you don't let your desires overrule your loyalty to your wife, even knowing that she might be naked with John as we speak. Sorry, I know that's blunt, but here you are...not taking advantage of...me." Lexi paused indicating her form with her hands. "You know I'm not going to say no, you know I'm yours to do with however you like, you know I'll never tell anyone, especially your wife. But you still are not going to compromise yourself. So, I'm going to have another drink since I'll need to get myself drunk so I'll be easy when I take myself tonight." Lexi waved to the waiter.

"Whew. I guess I'm going to have one to after that." James said. "You always this honest?"

"You obviously won't be any help," Lexi laughed, "but, tell me, if you were single, or if you didn't mind cheating, would we be sitting here talking?"

"You know the answer to that. So, what is it about Davenport that he seems to get what he wants, who he wants?" James asked with a pain in the pit of his stomach.

"Are you changing the subject? You know why he gets who he wants? He doesn't quit until they say yes. I think he gets more pleasure out of the chase than actually screwing them." Lexi replied thoughtfully.

"I would have thought he gets more pleasure out of...well, the pleasure. What? He likes wearing their resistance down?"

"Yeah, and seeing them go from a total no to them giving themselves to him freely. I think he likes seeing them figuratively, if not literally opening up to him. The cake is when they open their legs and offer themselves to him, everything after that is icing." Lexi said. "Are you bothered that John is working on your wife while we are out here?"

"Yes, I am, but there's nothing I can do about it, is there? I can either think about it or block it from my mind." James said sadly. "But, you said you've slept with him and...."

Lexi laughed, "And I'm not really an unwilling partner, you are suggesting. No, we have fucked quite a few times, and we both enjoy it. All his conquests seem to come back to him. I hate to say this, but if Anne sleeps with him, she will be comparing your penis to his every time you put it in her."

James groaned, "So he has a big dick, so what? What about love and passion?"

"God! You are really naïve, aren't you? During sex, love has very little to do with it, though passion plays a huge role. It's all about the level of eroticism, enhancing the passion. What was it about the first time you had sex that made it so special? What about when you fucked your girlfriend and she insisted that they do it in her parents' bed? It was the added eroticism, enhanced passion...was it forbidden? Risky? When John takes a married woman, she is opening herself up not just to his big dick, but to all the risks and dangers that come with being with a man who is not her husband - and she often does things with him that she never would do with her husband...you. They screw him and when he cums, they eagerly suck his dick until he is hard again and climb onto his hard cock and ride him some more. When did Anne last do that to you?" Lexi said looking James in the eye.

"I can see that. It scares me thinking she may crave that level of eroticism, passion. She likes to tease and get men aroused, but I don't think she's ever cheated on me."

Lexi chuckled, "That you know of. Face it, there's all levels of cheating. She could have ground her pussy into some guy's hard on on the dance floor, let a guy squeeze her ass, let him feel her boobs. That could be cheating, or it could be foreplay for later and you are the winner. Nothing is black and white. I know some of those women get home from being with John and their husbands get off fucking their sopping pussies. Is that cheating when their husbands encourage that? Only you can define cheating. You asked about John's dick? Finish your drink, I want to show you something."

James laughed. "I thought that was my line. Ok, where to?"

Lexi winked at him, "Come up to my room, honey. You'll see."

When they got to their adjoining rooms, James said, "Hang on, I have to stop in here, I'll knock on the connecting door when I'm done."

"Ok, go pee in your bathroom, I'll just open the door on my side." Lexi laughed.

James knocked and opened the door and found Lexi sitting of her bed with her hand behind her back. "Ok, what did you want to show me?"

"You asked about John's big dick?" She slid her hand from behind her back holding up a fat clear acrylic foot long penis. "This is why I keep going back to John, this is why so many other women go back. They may feel tremendous remorse, but a week or two later, they call him up and arrange to have their pussies stretched to the limit."

"No way, there's no way his cock is that big." James sputtered. "And, there's no way that would even fit inside of you, let alone Anne."

"You would be amazed what women would do to make this fit. And, yes, this is exactly the same size as John's. In fact, this is from a mold I took and sent off to have made. Thank God for Viagra since he had to maintain his erection for quite a while, not that he had too much trouble since a girlfriend and I entertained him." Lexi stroked the huge shaft while she told him this. "We did both get him to fill us up after the latex mold hardened – all the way in, if you are wondering, and my girlfriend is not much bigger than Anne."

James looked at the billiard ball size head and the thick shaft and imagined Lexi taking all that cock, and felt his cock twitch thinking about Anne with her legs opened wide.... James shuddered and said, "I cannot even imagine."

"Watch." Lexi said as she slipped her shorts and thong off. She grabbed a vial of gel and squirting it all over the head, she proceeded to lube the entire shaft. "Stay there and watch, I know you want to see this." Lexi said when James started to back away staring. She opened her legs wide and pushing the glistening head against her obviously aroused labia, she worked the head into her.

James was stunned and the abrupt display of nudity. He couldn't take his eyes off her cleanly shaven vulva and the small dark patch of pubic hair on her mons. His cock ached to be free as blood rushed into it.

Lexi kept her eyes on James as she pushed the massive shaft into her, watching his unblinking attention on her vagina being stretched wide and the length getting deeper and deeper into her. When it was as deep as it could go she released a satisfied groan and was happy to see a large tent in James' pants and a wet spot forming. "Oh God, this feels good." She moaned as she drew it all the way out before slamming it back in, "Could you at least play with my tits as I do this?" She panted.