Secret Santa

The next few dates were similar. They would start kissing and move on to groping. It got to heavy petting until Theresa put a stop to it. However, the weekend after, Theresa couldn't stop it. She didn't want to. She needed release and enjoyed the chance to. Theresa had three wonderful orgasms that night. Robert was exhausted after two. She could have gone on and when she turned to Robert to continue, he was fast asleep.

Theresa enjoyed her relationship with Robert. Then four months into the relationship, Theresa noticed that Robert wasn't as attentive. He became more selfish in bed. A couple of weeks later, she saw the signs. Robert was dating someone else and he was being clumsy about hiding that fact. He would tell her he has a meeting but not get home until late. When she called his office, his assistant would tell her he was not in that day or he had gone for an extended lunch.

Finally, two weeks later, she confronted Robert. He did not deny it. He simply packed up his things and left. Theresa was crushed. She thought it was going somewhere. She cried all evening. In the morning, she cried some more in the shower.

She went to work, avoiding the coffee shop.

Susan walks by Theresa's office and glances in. She sees Theresa crying. Susan stops and walks into her office.

"Theresa. What's wrong, honey?" Susan asks.

"We broke up last night." Theresa says as she tries to choke back the next sob into her tissue.

"Oh honey, I'm so sorry!" Susan says and walks over to Theresa.

She pushes Theresa's chair so that it swivels Theresa to face her. She puts her arms around Theresa and hugs her.

"What happened?" Susan asks as she pulls away Theresa.

"He was seeing someone else."

"That bastard."

"I should have known, you know." Theresa says as she wiped some more tears from her eyes.

"How could you have known?"

"This last month, he has been more distant. I've called him when he had said he'll be in long meetings and his secretary tells me he's out for the day or he is at a long lunch."

"That bastard." Susan replies again.

"He didn't even deny it last night!"

Susan hugs Theresa again as she began to cry once more.

"I thought it was going to go somewhere with him, Sue."

Susan patted Theresa on the back, "I know. I'm sorry."

Theresa cried some more. Susan just held her.

A few minutes later, Theresa pulls away. She wipes the tears from her eyes.

"Thanks Sue. I'm sorry to be like this."

"Hey, it's not a problem. Sorry that the guy is such a jerk. Can't believe that men would do that to women."

"I don't think all men would do that."

Susan laughs. "Oh? Name one."

"I can't think of one right now. But I'll tell you when I do."

Susan pats Theresa's arm and nods, "Okay, I need to get going. Will you be okay?"

Theresa nods and says, "Yes. Thanks again Sue."

Susan nods and walks out of her office.

That morning did not go so well for Theresa. For some reason her computer kept on crashing. She put a call down to Jack but his line was busy. So she called the head of the IT department to put in a request for service.

***

That was a month ago. Since then, they've talked every day and at least once a day. Jack was still nervous around Theresa and has his occasional lapses into incoherency around her but he was doing much better. Every Friday throughout the month, Theresa would go and say goodbye to Jack. Every time, she would give him a hug and a light kiss on the cheek. And every Friday night, Jack would go home and relieve himself. Every single time it was an intense experience.

Monday morning, Jack sits at his desk and looks up at his screen as the alert for new email comes in. Jack clicks on the message and reads. It is a note to all the office workers to see Susan about the annual 'Secret Santa'. The gifts were to be $20 and under. The names will be drawn at random. All those wishing to participate will need to contact Susan. The email also went on to detail where the event would be held. As usual, it will be held at the company Holiday party. The party is to be a week from today.

Jack picks up the phone and dials Susan's number.

"Hi Susan. It's Jack."

"Hey Jack! What's up?" Susan asks.

"Susan. Can you put me down for the Secret Santa?"

"Of course." She says as she types away. "You're in now."

"Oh and Jack." Susan says.

"Yeah?"

"Like the last two years. There's the secret executive Secret Santa."

Jack laughs.

***

The last two years, Jack was invited to the all secret executive Secret Santa. This consisted of the usual exchange of names and a gift. The people involved are the pool of executive assistants and a few others from the different departments. Of course, this is an event that is kept from the others in the company and HR. There was nothing serious that happens. The rules for this Secret Santa is that it has to be sexual in nature and the spending limit is $75 dollars. The only two other differences; one is that there will be a giver and a receiver – to be determined at random by Susan. The second, depending on the gift, the receiver has to wear it or use it. And, not everyone is a giver and receiver. The pool of names is divided in half and randomly selected to be a giver or receiver. Once selected as a receiver, their name goes to a bag where the givers must select a name. Everyone knows it is good-natured ribbing.

The first year Jack was inducted into this, he was nervous. Jack was a giver that year. He ended up just getting some expensive lipstick since he wasn't sure what to get or what was to happen when the item was presented. That year, his gift was to Rose. He had to apply the lipstick to her and afterwards, she kissed him. It was a fun and almost friendly kiss that lasted a few quick minutes. But the few minutes was long enough to get him aroused. Rose felt his arousal and teased him about it. It was a good-natured teasing so Jack wasn't too embarrassed. Jack still laughs whenever he passes by Rose and she would make ‘kissy’ faces at him.

The second year, Jack was designated as a giver again. He picked out Susan's name. Jack found a nice silk nightie for her. Susan squealed with delight as she opened her gift. Susan had run into her office and quickly changed into her nightie. She came out and walked over to Jack. Someone turned up the music and Susan gave Jack a nice little lap dance. Jack laughed but was nervous throughout. He knew he would not remain calm long.

At the end of the song, Susan asked Rose to borrow her lipstick. Everyone laughed and Jack quickly excused himself quickly before she could apply the lipstick. That caused everyone to laugh more.

***

Jack laughs into the phone, "Am I giver again?"

"Nope. You're receiver. Finally going to get some eh?"

Jack laughs some more. "No thank you, the last two years I got enough."

It was Susan's turn to laugh. "Well, good luck hon."

"Thanks, Susan." Jack replies. "Oh and I was wondering if maybe..."

"…If maybe Theresa has joined the executive Secret Santa?" Susan finishes for Jack with a little chuckle.

"Um. Yeah."

"Not yet, but I'm sure she will. I'll let you know." Susan says.

"Great. Thank you."

A couple of hours later, Jack received an email from Susan letting him know that Theresa has also signed up for the executive Secret Santa. By the end of the day, as Jack is packing up for the day, he receives a call.

"It Support. Jack speaking." Jack answers.

"Jack. It's Theresa." the voice says.

"Oh. Hi Theresa! How can I help you?" Jack asks as he fights to control his nervousness.

"Actually, it has nothing to do with work. It's a personal matter." Theresa asks nervously.

"No problem. What do you need?" Jack asks.

Theresa went on to describe what she needed and how she's been going to all the software shops around with no success. Jack took down the name of the software and told Theresa that he should be able to find it for her.

"Oh and Theresa." Jack says nervously.

"Yes Jack?"

"I hear from Susan that you've joined the executive Secret Santa."

Theresa laughs a bit nervously. "Yep. I've joined although it is a bit strange."

"Yeah. It was awkward the first time I joined too."

"Oh? Were you a giver or receiver?" Theresa asks.

Jack could not stop himself so he jokingly says, "Why Theresa, I'm surprised you ask that. You don't know I enjoy giving and receiving?"

Theresa laughs over the phone, realizing the innuendo.

"Actually, I gave both years. The first year, I gave Rose some lipstick. And the second year, I gave Susan some silk nighties."

"Oh? I did not hear about that. Maybe I should ask Susan about that."

"No!" Jack blurts out.

"No?" Theresa laughs, "And why not?"

"It's embarrassing."

Theresa says, "Oh?"

"Say, are you a giver or receiver?" Jack asks quickly, changing the subject.

"I'm a giver."

"Who'd you get?" Jack asks.

"I don't know. Sue hasn't told me yet. She said not all the givers and receivers have been chosen yet. Are you a giver again this year?"

"No. Actually, I get to sit back and receive this year." Jack says.

"So what would you want if I am to give you?"

Jack pauses a second to think. His mind frozen but he tries not to blurt out anything from his weekly fantasies. Then he says, "Well, aside from an evening with you, I'm not sure what I'd want. So my answer would be -- surprise me."

Theresa quickly asks, "Now are you saying an evening with me is worth only 75 dollars?"

Jack blushed and quickly says, "Well... I... you know what I mean."

Theresa laughs at Jack and says, "I do. I'm just teasing Jack."

She then surprises herself and continues, "Well Jack, what would you do with an evening with me?"

Jack blushes some more as he becomes instantly aroused.

But Jack says to Theresa in a husky voice, "Well Theresa. I would give more than I receive."

Theresa shivers at those words then smiles to herself as she hears Jack laughing embarrassingly at the other end.

"Now that's a nice secret Santa gift, if I do say so myself. Okay Jack. We'll talk later. I need to run. And thanks for looking into that software for me."

"Okay Theresa. I'll talk with you later."

They both hung up the phone.

***

Theresa wasn't sure what it was. Maybe she's been feeling particularly lonely these past couple of days or maybe it was something else. Other than that, she was feeling pretty good about work. She had gone to the office and gotten several things done ahead of time.

Susan had called her and asked if she wanted to join another Secret Santa gift exchange. Susan went on to explain that it is a little different from the usual. In that it was more sexual in nature.

Theresa asked Susan a few things about it. She found out that it was a gag event that started several years back. At first, it was only with all the executive assistants. Their chatter and gossip has always been racy so they had decided to have this one event at the end of the year.

The holiday party was a great excuse and the Secret Santa was a perfect disguise for the executive Secret Santa. Theresa asked if it was still only women. Susan told her that now a few select men are asked to join. Susan laughingly explained that it was fun to tease them and watch them squirm. Susan cited Jack as an example of men squirming. Theresa asked about that and Susan told her about the last two events. She laughingly said to Theresa that Jack seems to get aroused by a single kiss or a thought of a kiss. Theresa laughed and in the end, agreed to join it. Susan told her that she has come up as a giver. Susan would get back to her on who her receiver would be. Theresa hung up the phone, a little excited about the executive secret Santa.

As she was hunting around for her next work item, she found a post-it to herself. It was a reminder to ask Jack about the piece of software for her nephew. Theresa picked up the phone and dialed Jack's extension.

As the phone rang, she realized that enjoyed talking with Jack. Their last few weeks of conversation had been easy, nice and informative. She had spoken with Susan about Jack. Susan had nothing but good things to say about him. She even mentioned that he was fun to tease. Theresa had asked Susan to expand about that but all she would say is that unlike other guys, he can be teased and he won't get all 'huffy' and walk around with a bruised ego about it.

So when Jack brought up the executive secret Santa, she thought back to the conversation with Susan. Theresa was enjoying herself with the fact that Jack was nervous about the executive secret Santa's in the past. She made a mental note to ask Susan about it.

At the end of the day, she hadn't heard from Jack. She was a bit nervous because Christmas was getting closer. In a couple of weeks in fact. She decided to see if Jack had any luck with it. If not she'll have to spend the weekend going to the malls to see if they have it. She headed to the elevators and got off the floor where Jack's cubicle is. She walks over to his cubicle and hears that he's on the phone. She quietly stood outside the cubicle waiting for him to get off the phone.

"Bill, it's Jack, man."

"Did you get my message earlier?"

"Cool. So you do have it?"

"Great!"

"Bill, stop playing. I really need it."

"Anything."

"Yep, it's for a friend here at the office."

Theresa guessed Jack was talking about the software she had asked him about. She steps back from the entrance of the cubicle and hovers next to the wall.

"Yeah, it is for a 'she'."

"I'm desperate. I'll do anything."

"Well, yeah. I'm off those two weeks."

"You're kidding right? Two weeks for the software?"

"Yeah. I really like her."

"Yeah. She's also really hot."

"What? I don't know. She's got really nice hair, great personality."

"Yeah, she's got great legs. And a wonderful smile. Her eyes are to die for."

Theresa blushes to herself and decides to stop the conversation. She didn't want Jack to trade his vacation for whatever Jack's friend is asking for.

"Alright. It's a deal. I'll pick it up Thursday after work okay?"

"Great. And Bill, I really appreciate this."

"Yeah, she's a sweet person. I'd try to do anything for her."

"No. I'm not." Jack says quietly. "Listen. I need to go. I'll see you Thursday okay?"

"Yep. Later."

Theresa stops herself from walking in and turns around. She quietly walks back to the elevator and heads back to her office.

The part of the conversation she heard told her two things. Jack was sacrificing is two weeks off for the software she asked for. And the second thing was that Jack likes her. She thought about it for a minute and realizes that she likes Jack too. She smiles to herself as she recalls her conversations with Susan now. Susan had been trying to get Theresa to talk with Jack more. Normally, Susan is a straightforward person but now in retrospect she realizes that Susan was trying to tell her something.

Theresa saw that she had a voice message and picked up her phone. She called in and heard that it was Jack. He had said that he got her the piece of software that she wanted. He'll have it for her on Friday, the night of the Holiday party.

She hangs up on the voice mail and quickly dials Jack's extension.

"It services. This is Jack." came the voice.

"Hi Jack."

"Theresa!" Jack answers excitedly, "What can I do for you?"

"Jack. I got your voice mail. Thank you."

"No problem." He says.

"I hope it wasn't too much trouble." She asks nervously.

"No trouble at all. I don't mind, especially since it is for you."

"Oh, that's sweet. Thank you." Theresa says.

Jack laughs nervously at the end and asks, "Hey, do you know who you're giving to on Friday?"

"I'm not sure. Let me see if Susan left me a note."

Theresa turns to her computer and checks the new mail. She sees a note from Susan and opens it.

"Yep, she left me a message. Looks like my receiver is Tom."

"Oh." Jack said a little disappointed.

"Sorry, Jack. No evening for you." Theresa teases.

Jack laughs and says, "Well, there's always next year!"

Theresa smiles to her, "That's right."

"Okay, I should let you go. It's after five." Jack says.

"It's okay Jack. I really enjoy talking with you. Thank you again. I'll see you tomorrow."

Theresa hung up the phone and got her things together and left the office.

***

That evening, Theresa had a hot bath. She dozed off in the bath and dreamed of Jack.

She and Jack were kissing. They were kissing slowly and softly but passionately. She moves her hands up and down his back. Her hands would wander down to his ass and she would squeeze him. She could feel his cock, hard, against her stomach. She wanted to kneel down and pull his cock out and into her mouth but she enjoyed their kissing too much. She feels his lips moving away from her mouth and move further down. Her hands move from his ass up to his shoulder then to his head. His lips gently took her nipple into his mouth. She sighs as she feels him gently sucking on her. She presses his head against her as her nipple hardens. She could feel his hands moving down from her back to her ass. She sighs as he lets go of her nipple. She could feel him shifting over to her other nipple. She pushes her breast forward to meet his lips as his mouth surrounds her other nipple. Her nipple hardens instantly in his mouth as she felt his hands move from her ass to her waist. She could feel him pulling her down. She lowers herself to sit on the couch. His tongue moves around her hard nipple as his hands move down from her hips to her thighs. She feels his hands moving along her thighs. She gasps lightly as she feels his fingers touch her. His fingers moves lightly along her pussy and gently spreads her. She could feel his finger tip play with her clit. Her body moves, hips grinding forward slightly as he teases her. His mouth releases her nipple. His fingertip moves around her clit. She tilts her head back slightly. She moans lightly as she feels his lips touch her neck. His fingertip moves from her clit over to her entrance. She gasps and reaches down to touch his hand as his fingers enter her. She moves with the movement of his fingers. She touches herself as his fingers glide into her. Her fingers move over her clit as she rubs herself. She feels his teeth lightly grazing her neck and she shudders some more. She moves faster, feeling the wave of pleasure flowing and warming her entire body. She feels him moving his lips down her. She shivers again as she feels Jack's fingers moving slightly faster in and out of her. She moans and looks down. She sees his lips just as his mouth closes over her nipple. She moans and moves faster, urging his fingers to move faster. She shakes as she feels the wave starting. It moves from her stomach and pulses out. She opens her mouth to scream as she wakes up. She continues to orgasm in the bath. She reaches down to touch herself as she finishes it up. She sighs and lies back against the tub. She smiles to herself as the glow of pleasure settles on her. She thought of Jack again. Yes, she found Jack attractive.

***

The next couple of days went by quickly for Jack. He had spoken with Theresa and she had been more friendly than usual.

Thursday came around and for Jack the day could not have gone any slower. There were a few major catastrophes involving the mail server and later the network server. It was all handled in a timely fashion and Jack was relieved. As Jack was packing up to head over to Bill's to pick up the software, there is a knock on his cubicle wall.

Jack turns to see Theresa standing there. He smiles at her.

"Hi Theresa."

"Hey Jack." She smiles at him.