tagGroup SexSanta Favor

Santa Favor


This is my entry in the winter fun stroy contest. I hope you enjoy this fun little Christmas yarn. Vote early, often and of course, 5's!


"Roooooberrrrrrt!" Diana, one of the engineering secretaries, cooed in a melodic tone as she stepped into my office and let the door closer push the steel door closed behind her. She stepped to my desk and standing straight legged, bent at the waist to rest her elbows on my desk, the creamy expanse of already exposed cleavage of her big thirty-eight D's growing even more as her breasts tried to push up out of the deep V neck of her powder blue dress.

"Oh geez." I groaned softly.

"What? You aren't happy to see me?" she asked with an all too fake pout.

"Diana, any time you come in with that tone, you want something that you know I'm not going to like to do."

"Awwww. That's not fair. I haven't asked you to do anything that horrible, have I?" she asked in a very sultry tone.

"Oh, not at all. What was it, seven blind dates before the river fiasco?" I asked.

"That was six months ago, and it wasn't my fault she didn't know how to canoe. Besides, you got plenty of reward," she said with a grin, moving one hand to the deep V of her dress and gently stroking her fingers across her right breast, gently hooking them in the slick material to expose even more of her creamy skin. "After all, that one time she flipped both our canoes you got a really good look at these ladies, didn't you?"

"Somehow looking at another man's wife's tits isn't exactly payment for having to endure her antics," I said with a frown.

"Oh come on. It wasn't that bad, was it? I mean she wasn't bad looking, was she?"

"No, no. She wasn't bad looking. I just wasn't all that sure that I wanted everyone on the river to watch me having sex with her, which she didn't seem to care about."

"I know. But even you have to admit that once you got that nice flash of my tits that bulge in your swim suit was awfully attractive. That's probably why she spent so much time flashing you after that."

"Yeah, I know. But if I wanted a quick fuck, I'd go pick something up at the bar."

"Honey, Mary's been gone almost a year and a half now. Isn't it time you found someone that could be more than just a quick fuck?"

"We've been over this before. We were married for over twenty-five years, that's not something you just replace with any old person," I answered her, trying not to let the frustration I felt at that moment to seep out in my voice.

"Honey. You also know that if I wasn't already married I'd be climbing all over you. You're sweet, caring, kind, strong, intelligent, and from every account I heard from Mary before she got cancer, one hell of a good lover in bed! She asked me to make sure you didn't spend the rest of your years alone, and that's all I'm doing!"

"Yeah, I know. She told me she gave you that job and that I was supposed to go along with whatever you asked me to do. I just don't feel like what she and I had was exactly something you replace."

"No one is asking you to replace it. She just wanted you to find someone that would complement you and she hoped that you could find happiness again after she was gone."

"Yeah, I know," I said with a sigh. "So who's the date this time?"

"Now who said I was setting you up with a woman on a blind date?" she asked, the fake pout showing up again.

"Right. No date. You just come in here wearing a very tiny skirt, showing more of your tits than any sexual harassment limit would allow, and try to seduce me into doing something you know I wasn't going to want to. What could be more natural?"

"Oh, that's cold. All I want is for you to help me out with something."

"And if I say no?"

"You've been dying for me to flash you my pussy. It's freshly shaved and I don't have any panties on!" she said with a crooked grin.

"So you want to bribe me with sex?" I asked. "Maybe I should call HR and complain about sexual harassment."

"Yeah, right. And that bulge in your pants means what exactly? You know we can't fuck. We've been friends way too long to take this kind of play for anything other than what it is, teasing and playing."

"Yeah, right. Okay. You obviously went to a lot of trouble to try and convince me to do this. What do I have to do?"

She smiled broadly at me. "All you need to do is to come over tomorrow around one and play Santa for a little party I'm having."

"Santa? Seriously? How am I supposed to play Santa?"

"Oh, I have the suit and everything. All you need to do is show up and hand out a few presents. Now that isn't so bad, is it?"

"I have the distinct hunch that there is a whole lot more to it than that. Come on. What's the catch?"

She pushed up off the desk and stepped around the side closer to me, settling her firm, round ass on the corner, her right leg lifted off the floor so her thigh was pointed toward me, her knee bent to hook the high heel in the handle of a desk drawer, the other leg reaching straight toward the floor. She looked down at me with a crooked grin. "You aren't really going to make me pull out all the stops, are you?" she asked, sliding the hem of the skirt up a few inches and pushing her right knee closer to my desk to spread her legs a little farther.

"Come on. You know I'm not trying to look at your pussy. You're married!"

"And if I wasn't, I'd be crawling all over your body right now, trying to get the cock making that huge bulge into me," she answered, hiking the skirt up slightly higher, the dark shadow caused by the skirt's material the only thing keeping me from actually seeing her pussy.

I paused a few breaths, wondering if she was really going to pull it farther up and then shook my head and sighed. "Okay. You win. I'll do it," I said with a sigh, wishing for a few moments that I'd let her take this a little farther, friend or not.

"Great!" she said with a huge grin. "I knew you would."

"Why? Because you were going to show me your pussy?" I asked.

"Oh honey. You should know by now that I'd never try to bribe you that way!" she said, sliding off the desk, letting the skirt slip up her legs far enough for me to clearly see a pair of black panties covering her pussy that showed less than the bikini at the river over the summer. "Now, come to the back door when you get there. One sharp!" she said with a smile.

"You're horrible," I said, shaking my head.

"Oh honey. I'm anything but," she said, stopping half way to my office door. She looked over her shoulder at me and then reached up under her skirt and pulled down her panties, bending at the waist again to push them down her legs. She stayed bent over, as she lifted one leg and then the other to step out of the black briefs, the short skirt pulling so high up that I could see the curve of her ass cheeks and a little glimpse of full, round pussy lips pushing out between her legs toward me. She stood that way for several seconds, letting me stare before straightening up. She lifted the panties to her nose and sniffed before tossing them across my desk into my lap. "Trust me, I'd never tease about something that turns me on this much," she said before stepping to the door and opening it, disappearing out into the hall.

I picked up the black satin panties to stuff them in my desk drawer and couldn't help but notice how wet the crotch was. I briefly lifted them to my face and drew a deep breath, inhaling her scent. Yeah, if she wasn't married, twenty years younger than me or not, I'd be trying to get into these panties. She and my late wife had been good friends for years, but that didn't stop me from thinking what it'd be like to undress her. I mean I'd seen most of her body at this point, given the tiny bikinis she always wore when we would go to the lake or canoeing or swimming. Sometimes I felt like she really wanted me to see her naked. And now, I'd seen everything but a front view of her pussy.

Six months ago I'd seen her bare tits after the less than substantial bikini top slipped off both full, round breasts when we all dumped on the canoe trip. Now she'd flashed me a back view of her pussy. I wondered if she really intended to flash everything at me at some point. Not that I'd complain, exactly, but she WAS married. Jack was missing from the scene all too often, being a field sales guy, but that didn't give me or anyone else the right to tee off on his wife. As much as I wouldn't mind seeing her naked, I wasn't going looking for it. I shook my head and went back to work, wondering what kind of trouble I had just let myself into. I suspected there was more to this Santa thing tomorrow than she was telling me, but the only way I was going to find out was to show up.

I arrived at Diana's house, just a few minutes before one. I wasn't surprised to see her husband's car gone, probably off on the road again, but I was a bit surprised to see several other cars in the drive that I didn't recognize. It took a few moments to realize that they probably belonged to whoever was at this party of hers. I parked and walked through the light snow around to the back of the house.

Diana met me at the back door in a tight fitting red dress covering much of her five and a half foot frame, with a four inch wide, white fluffy, trim around the hem. She had white stockings that extended up from her white six inch heels up on her thighs, leaving a six inch gap of creamy, white leg between the bottom of the short skirt and the stockings. The front of the dress, from her navel to the top of her full, round tits was fastened together with a red string, crisscrossing back and forth, leaving a strip of creamy white skin visible between the two halves of the front of the dress, making sure that anyone looking knew she was braless. Not that the jiggling of her full tits inside the dress didn't already prove that.

"Holy crap!" I said as I looked at her in the sexy dress.

"You like?" she said, doing a quick pirouette for me. "It's my Santa's helper dress."

"It's one hell of a dress! I'd have to guess that Santa wouldn't finish his rounds if he really saw you in that." I said as I looked her up and down.

"Oh, now that IS a compliment!" she grinned, wiggling her chest slightly to give me just a few moments more pleasure before continuing. "Now come with me. You can change in the guest room," she said, taking my hand and pulling me across the kitchen toward a hallway that I had been down many times over the years. She ushered me into the small guest room. "You can change in here," she said as she stepped to the closet.

"Damn, it's warm in here." I muttered as I peeled off my heavy winter coat.

"Well, then you better take off everything or you might roast in the Santa suit," she said with a giggle.

"Yeah, right," I said with a frown, as I started pulling off my long sleeved shirt.

"I forgot the suit, it must still be in my car. I'll be back, you just go ahead and get undressed. I'll be right back," she said before stepping out and closing the door behind her.

I pulled off everything but my t-shirt and boxers, leaving my clothes in a pile on the bed before she came back. She handed me a small plastic bag. "Here you go honey!"

"What's this?"

"You're Santa suit," she said with a grin.

"Seriously?" I asked as I opened the bag and looked in. "What's this?" I asked incredulously as I pulled out a pair of bright red fluffy shorts with fluffy white trim and red suspenders. "This isn't a Santa suit. It's a stripper's outfit!"

"Yeah, actually it is," she said with a crooked grin. "Couldn't get a regular one, they were all reserved, but I figured you'd look damn sexy in this!"

"I am NOT playing stripper for you!" I said emphatically.

"You're well-endowed enough to get the job done," she answered, still giggling at my reaction.

"I'm not playing stripper! No way, no how!" I answered her.

"Okay, okay. No strip tease. Just wear the suit and give out a few presents, okay?"

"No. Not happening," I responded resolutely.

Diana looked at me, a tinge of anger flashing across her features. In a hushed voice she almost growled at me. "Robert. Your wife was my best friend, and she made me promise to help you find someone to be with so you wouldn't be alone. She knew damn well that you'd refuse to open your heart and even think about letting someone back in. She knew how hard it was for you when she was out of the country for months at a time, but she also enjoyed how good you two were when she came home. She made me promise to help you find a woman that was playful in that same way. She knew that if you could at least find a friend to enjoy some of that activity with, you might learn to open your heart again. I'm not about to fail on the final, dying wish of my best friend, so put these on and come play Santa!"

"Geez," I said quietly. "I know she wanted you to fix me up, but I'm just not ready to replace the one person that was the center of my life for so long."

"I'm not asking you to find a new love of your life. I'm asking you to enjoy the company of a good woman and see what happens after that. Now put the shorts on and come out! No more excuses!" She said stepping past me, picking up my pants and turning to walk out of the room with them. "And get rid of the t-shirt too."

"I suppose you want me to lose the boxers as well?" I said jokingly.

She stopped and turned her head to look at me, one hand on the doorknob to open the door. "Now that you mention it, yeah, I wouldn't mind. Want me to wait around while you change?"

"Seriously? Wear nothing but the shorts? I'm not playing stripper!" I said again, shaking my head.

"You don't have to," she said stepping back over to me, her face softening. "It isn't THAT kind of a party anyway. Trust me. But if it was, you'd still do a damn good job at it."

"So, just exactly what kind of party is this anyway?"

"A lingerie party of course. Think a dozen women all trying on sexy little nothings," she said with a crooked grin. "Oh and don't forget the toys," she added.


"Oh yeah. Vibrators, dildos, a couple even tried on strap on dick, just for fun," she said with a giggle. "Oh yeah, that definitely did it," she said, reaching out and running a finger across the bulge suddenly growing in my boxers, making it twitch and making me jump back half a step "Yeah, definitely lose the boxers!"

"You're impossible," I said, shaking my head.

"Uh uh. Not at all. I'm just doing exactly what Mary wanted me to. But just because I promised to make sure that you didn't try to become a monk or something doesn't mean I wouldn't mind standing here and watching you change. I've kinda been dying to see what Mary raved about so often."

"I don't think that'd be right, with you being married and all,' I said, wondering if she was serious or just joking again.

"Maybe not, but I still wouldn't mind," she said as she opened the door. "I'll wait outside and...yeah, definitely lose the boxers!" she said as she stepped out and closed the door behind herself.

It didn't look like I was going to have much of a choice. I could sit in here the rest of the day or put up with another attempt at her match making. I knew she was only trying to help, but so far her attempts at blind dates hadn't just worked out particularly well. With a sigh I pulled my t-shirt off and started stepping into the shorts. I paused for a few moments, thinking about what she said about the women trying on lingerie and shrugged. I made a very similar promise to my wife before she passed, promising to go along with whatever Diana asked, no matter how outrageous. I pushed off my boxers and then pulled the shorts on slipping the suspenders over my shoulders. I felt ridiculous. Not that I hadn't worn some rather interesting outfits when doing a little role playing with my wife, but I hadn't ever quite done this kind of thing with a stranger, let alone a room full of women I didn't know.

With more than a little trepidation, I picked up the small red bag of presents she had left next to the door when she brought in the costume and opened the bedroom door. I found her standing outside the door, leaning against the wall, her arms crossed impatiently.

"Good. Now, at least try to look like you're having fun, okay?" she said with a frown.

"Yes ma'am." I said, rolling my eyes as she looped her arm in mine and pulled me along. I felt ridiculous wearing nothing but the red shorts and white crew socks. I let her lead me down the small hallway and turn the corner to step out into the living room. Five very good looking women were sitting on the sofa and overstuffed chairs around the coffee table where several empty or partially empty wine bottles and glasses were sitting on the table in front of them.

"Ladies, I promised a sexy Santa! Here he is!" Diana said brightly as she led me to a chair sitting by itself in front of the table across from the sofa while the women clapped and one whistled a high-pitched wolf whistle at me. "Ladies, please. Robert agreed to play Santa for us, he is NOT a stripper! Although I for one wouldn't mind watching him do that, we're not here for that."

"I know," a tall, willowy, redhead sitting on the sofa offered. "But you have to admit, he has the outfit for it! Damn!"

"It's all I could get for a Santa suit," Diana answered. "Just a lucky coincidence that he looks good enough to wear it."

"Yeah, for sure. Nice abs for a guy that you said was getting a little older!" A slightly heavier set woman said, her black long sleeved dress exposing a lot of cleavage, the unusual dress design allowing her black lace panties to show as she sat on the sofa across from where I was supposed to sit.

"Got that one right Tiffany!" the redhead agreed, each move she made making the sequined top of her strapless cocktail dress shimmer in the living room lights

"Now ladies, let's behave," Diana said. "Robert, this is Elaine," she said, motioning to the woman sitting in the overstuffed chair to our left.

Elaine stood up and stepped closer to me, extending a hand to shake. I guessed that she was about ten or so years younger than my fifty. Her slender waist, long brown hair that looked like it went at least to the middle of her back, deep green eyes and full, round tits that were showcased in a short red dress that had a scoop neck of loosely folding material, exposing an expanse of lightly tanned skin from her neck all the way to her bellybutton. There was a single wide red strip of material around her neck, attaching to the flowing top with two large brass rings, keeping the material covering what looked like a pair of very full round breasts covered but otherwise unrestrained. The rest of the material of the dress clung to her hips and lower, extending barely below the curves of her full ass.

"Hello!" she said in a sultry soft voice, dripping with desire and sensuality as I took her hand, its warmth flowing into mine as she held my hand firmly, her green eyes making and holding contact with mine for long seconds before she smiled softly and withdrew her hand from mine, leaving me slightly stunned.

"Um. Hi," I answered her awkwardly as she moved back to her seat.

"This is Jessica," Diana said, motioning to the woman sitting on the end of the sofa. She had on a red and black dress, but that's where the similarity to Elaine ended. Jessica was of African American decent, the significantly expanse of exposed skin was the color of heavily creamed coffee. Her jet black hair framed her smiling face in tightly curled little ringlets. She stood up and reached across the table to extend her hand to me, her red halter style top exposing the sides of her full, round breasts down midway to her stomach as she stood, As she leaned toward me to take my hand I could easily see even more of each, at least D cup, breast as the dress allowed her breasts swung free to push the material away from her body. As she took my hand she leaned across far enough that I could see that her back was bare and the top of the dress held in place by only a small thin string around her neck that was currently straining to hold up her large breasts against gravity.

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