Holiday Surprises Ch. 01

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Christmas Eve - Scott gets an unexpected double gift.
4.3k words
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Part 1 of the 6 part series

Updated 10/02/2022
Created 01/10/2008
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My eyes opened to the sound of the alarm clock going off, playing an annoying tune. I always leave it on a station I hate, so I get up and turn it off. I turned it off and rubbed my eyes, staggering to the bathroom to release my bladder with my morning hard-on. I laughed to myself, every morning was the same for most guys I assume, gripping the back of the toilet, attempting to aim my stiff prick down, trying not to piss all over the wall first thing in the morning. I suppose that's the price we pay for peeing standing up.

After brushing my teeth and throwing on a tee shirt and cargo pants, I walked out to the kitchen for some breakfast. It had been two days since Ann treated me to my Birthday romp on the kitchen table, and the memory still lived vividly in my mind. We hadn't watched the video yet. Heck, with yesterday's mad dash for last minute Christmas shopping we barely even saw each other.

I grabbed a box of cereal, milk, bowl, and sat down at the table to eat, where less than 48 hours ago I was lapping at Ann's slippery cunt. I shook my head trying to focus on the day at hand. It was now Christmas Eve, and I had some work to do to prepare the house for our annual Christmas party.

So I spent the morning hanging a few more lights on the house, setting up some large bows in plants and greenery Ann had requested, and getting the last two Christmas trees in from the garage. Following the list she left for me before she headed over to her sister's this morning I completed each task quickly.

Finally being done, I found myself in front of the t.v., with a beer, watching football, content to just relax and take in the game. Just then my cell phone rang. I knew it wasn't work, it must be Ann.

"Hello" I answered.

"Hey there sexy!" Ann's cheerful voice responded at the other end. "How's my chore-boy doing today?"

"You're chore-boy is done, and relaxing with a beer." I stated flatly, mildly annoyed with her condescending tone.

"Well, I was wondering if I could make one more last minute invitation?" she asked coyly.

"As long as we have enough food, and that invitation isn't going to my Mother, I don't care who you invite" I said plainly, getting bored with our conversation.

"Good, it's settled then" and the phone went dead. She just hung up. I stared at the phone a moment in disbelief, wondering what was up, and focused back on the game. "Whatever" I thought to myself.

I must have dozed off to sleep because when I awoke the sun was shining in through the windows and someone was kicking my foot.

"Wake up sleepy" Ann's voice was sweet now, waking me up gently.

"Hey gorgeous" I managed to grunt, clearing the sleep out of my head.

"Time to get ready for our party babe, our guests will be here any minute" she replied.

It was then that I noticed that she'd been home for a while, all the food was set up and she'd changed. She looked stunning. Her auburn hair was pulled up, the diamond earings I bought her last year for Christmas were dangling from her ears, and her body was enveloped in a skin tight red dress with a plunging neck line revealing the sides of both here ample breasts, she clearly wasn't wearing a bra. The dress stopped about mid-thigh, very sexy, red stockings continued down her sensual legs to her shoes, they were red and had a single buckling strap above her ankle with about a 4 inch heel, classy, but unmistakably sexy, she was nearly too sexy from a gathering of friends and neighbors. My cock throbbed at the sight of her.

I headed upstairs for a shower and change wondering what the party would bring. As I showered I envisioned Ann in her dress, I thought about jerking off, but decided I had no time.

I exited the shower finding clothing laid out on the bed for me. "My little Ken doll" I heard her voice in my head, as she's said to me several times. She enjoyed dressing me, I put up with it because I enjoyed her undressing me later, which she seems to enjoy as well, so I pulled on the black slacks, there was no underwear to be found, so I went without, and the bright red oxford shirt, red socks (nice touch), and black Italian slip on loafers.

As I headed for the door I took a look in the mirror, as I did, I noticed the package of ribbed condoms I picked up a two nights ago in the reflection over on the nightstand "interesting...what's she got in mind?" I thought to myself. I headed downstairs.

The party was in full swing when I got down there, there were Mark and Sara, our neighbors, talking to Judge Mitchell, a newly elected State Court judge, and old friend of Ann's father. I saw a few select people from my office, John and his wife Bridget, also Sally was there with her date for the evening, some long haired rock star looking guy whom I would later learn was named Digger. The rooms were filled with many other people I recognized, and some I didn't. I arrived in the kitchen to find Ann talking to an attractive blond girl who's back was toward me, and from the look of things, the conversation was rather intense.

Ann smiled when she saw me approach, "Hi Sweetie, you remember Alison don't you?" she said with a big smile crossing her lips.

Holy Shit! It was the waitress from the restaurant that couldn't keep her eyes of Ann the other night. She'd slipped Ann her number, and my sweet little girl had the balls to call her and invite her.

Alison turned to me, and stepped forward, closing our distance quickly. "Hello" she said politely, never breaking eye contact with me.

"Good evening, it's nice to see you again" I replied, noting how cute her face looked.

"I hope you don't mind Ann's last minute invitation, but I was very excited to get her call, and I wanted to see both of you again" she said, her voice was bubbly and light, and her eyes were giving me the once over.

The other night I thought for sure she was only interested in my Ann, but her advances toward me now had me a little confused. She clarified her interest momentarily.

"I hope my outfit isn't too racy from your 'up-town' crowd" she whispered in my ear.

I took my time taking a small step back to appreciate the view. Her tight cut blond hair was spiked again, framing her thin face and large lips. She had on tight red tube top stretched paper thin over her slight frame, making very apparent that her nipples enjoyed the cool air. Her tight stomach was bare, exposing her sliver of a belly button. She had on a black mini skirt that could best be described as a belt. So low on the top, it cut well below her hip bones, and so short, I'm sure if she bent over, she'd have nothing to hide. No visible trace of a panty line anywhere. He legs were bare, and her feet were clad in tall five inch stiletto heeled black leather open toes. She was thin, but incredibly sexy. My cock throbbed inside my pants, there wasn't much to hide without underwear on.

"You look..." I paused searching for the right words "like pure sensuality wrapped in a tight little package".

She smiled, gave me the once over again, pausing to look at the bulge in my pants. She leaned in closer and whispered..."You didn't need to say a thing, your little friend told me what I already knew." And she turned brushing her hand against my crotch so only she and I knew what just happened.

Holy Shit! I thought to myself, here was this 18 year old sexpot overtly coming on to me now, after toying with Alison on my birthday, I couldn't believe she was standing here in our kitchen! I also couldn't figure out how to hide my now impressive bulge. I was going to have to cool down and focus if I wasn't going to make an ass of myself the rest of the night. I grabbed a plate of snacks and made my way to the beer cooler, this was going to be interesting.

I talked with various guest throughout the night, had an interesting conversation with the Judge about Ann's father's drinking habits in college.

I formally met Digger, as formal as that could be. Three minutes into our conversation I was bored out of my mind until Digger spilled how he and Sally met. Backstage after one of his shows, she and two other girls had "blown" their way in to meet the band, and apparently, Sally our prim and proper receptionist, shared Digger with two friends, she stuck around to fuck him the morning after, and now here they were, a whole 2 weeks later, deep in love. "Sure", I thought, but laughing internally at what a whore Sally seemed to be outside of work. I'm sure she didn't intend for that to come out at the party.

I also talked briefly to Mark and Sara as the Jack Daniels was hitting me pretty hard, Mark and I talked about planning a block party for the 4th of July, but I couldn't stop staring at Sara's tight little 22 year old D Cups stuffed braless into her satin blue spaghetti strap dress. I think Mark got mildly annoyed and cut off our conversation as they headed home. "Bastard" I thought, she's probably going to smother him with those tonight.

It wasn't like I had anything to complain about. I watched Ann move graciously through the party, politely speaking with everyone there, always the quintessential hostess, but looking ravishing in her red dress. My cock perked up again as the alcohol was wearing off as I sat in silence content with watching her float through the room.

A body dropped onto the couch next to me, into me really. I turned to see who, and it was Alison, casually leaning into me. "Hi there!" she giggled.

"Well hello there Alison!" I replied; genuinely happy to see her. My cock throbbed once in my pants, thickening a little at her presence. "Still here, I though you'd have gone home by now?"

"Me, no way, your sexy girl wanted to make sure I stayed around for a while" she stared at me coyly, her hand moved to my inner thigh "in case anything.....comes up" she smiled.

My cock leaped again once, and all I could do was look at Ann. She was watching Alison's advances from across the room while holding a conversation with another guest. She gave me a wide smile, and a wink, I thought for a moment, and then Alison handed me a napkin.

Words in Ann's handwriting were written carefully on it. Alison just smiled, and moved her hand slightly up my leg as I reached for it. It read: "You get her first, but don't tire her out stud, I'll meet you upstairs in a little bit...Merry Christmas...All My Love, Ann"

Holy Shit, was I just given permission to fuck this young little minx? What was this about her getting seconds? Ann and I had talked about a threesome, but never done it. I knew she'd experimented in college, but no girls entered the picture since we'd been together.

I looked back at Alison. She looked at me, and whispered, "Meet me in your bedroom in five minutes", she gave my cock a squeeze and was off.

I sat there dumbfounded, looking at Ann across the room. I marked off ten minutes and headed upstairs myself. When I opened my door I couldn't believe what I was seeing. Alison was standing near the bed, the arms of her slight frame motioned for me to close the door, and when I did she immediately pulled her tube top over her head. Exposing her perky, yet tiny, little A cups, they were capped with little eraser-like nipples, pink and already hard. She motioned for me to come closer, as I did, she dropped her skirt to the floor, her nearly bare pussy exposed in the bedside light. Just a neatly trimmed blond strip was left above her lips, and the rest was shaven smooth. She stood before me naked with exception of the high heels.

"What do you think?" she asked giggling.

I looked up and down her teenage tight body, wondering what I had done to be so lucky. My cock stood rock hard, straining the thin fabric of my black pants, a spot of precum already forming at the tip. I didn't say a word.

"I think I know the answer already" she giggled as she stepped towards me and leaped into my arms wrapping her legs and arms around me. She whispered into my ear "I've never had a man inside me before..."

I almost dropped her, "You mean you've never been with a guy before?!"

"I've played with a few guys, and done lots with women and dildos, but I've never had a throbbing cock inside me, and Alison said you'd be careful and make my first time incredible for me".

I nearly came right there. She planted her hungry mouth on my lips and kissed me passionately. I reach around to hold her, gripping her tiny ass cheeks, feeling her wetness that had already spread form her little pussy to the sensitive skin of her most upper legs and ass.

"It does come with one condition from Alison, but I'll worry about that later." She whispered.

I don't even think I heard her, I was just thinking about this little virgin, tightly wrapped around my body.

As she kissed me, she began unbuttoning my shirt, she made it all the way down while still perched on my hips. She pulled the shirt over my shoulders and leaned down to kiss and lick my neck, then lower to my left nipple. She pinched it gently and tugged at it with her teeth as her hands lowered to my belt. My cock strained to be released as her hands worked my belt loose and my pants button and zipper now between her own legs.

My hands caressed her ass as she worked her way down my body, my mind reeling with what was going on. I walked her over to the bed and let her down, as I released her, my pants fell to the floor and I kicked them off with my shoes and socks. Before I could join her on the bed, she had positioned herself in front of me, laying on her back, her head dangling off the bed in front of my rock hard cock.

She didn't say a word, she just grabbed my ass and pulled my cock to her lips, taking me in instantly, she sucked and licked like a pro, expertly handling my cock. Her tongue running over every fleshy vein and ridge and sucking my balls into her mouth. She was able to take me deeply into her throat nearly cramming all of my throbbing pole into her mouth.

I reached down and gently massaged her breasts, my hand sliding lower to her already very wet pussy, bending over her we assumed a 69 position and I tasted her cunt. She was sweet, but slightly different from Ann, but tasty none the less. I lapped at her wetness hungrily devouring her lips, and flicking my tongue over her clit, she squirmed under my touch and moaned into my cock penetrating her mouth. I had her cumming in no time. She groaned loudly around her mouthful of cock when she came, her hips rising off the bed and sending a shower of girl cum spraying from her gash across the bed.

As her body began to relax, I stood up again, intent on watching her finish me off. But she pulled my cock from her mouth, and kneeled facing me, planting a wet kiss on my mouth, commingling her own cum juice and my precum in our mouths.

"I've never had a man make me cum like that!" she cooed as her tongue darted in and around my mouth, sucking her own juices from my lips.

"I want you" she squealed "I want you to fuck me"

With that I shoved her gently onto her back, grabbed her stilletos and pulling her ass to the edge of the bed near me, her legs spread out in both directions. "Are you sure?" I asked, she nodded quickly grasping my cock and guiding it to her entrance. Not wasting any time I pushed my cock into her, and she screamed "Oh yes!" My mind wandered for a second to the guests below, praying the music covered that up, then my mind snapped back to the naked teenager, barely an adult, enjoying her first cock inside her.

She was tight, very tight, and I didn't slide in all the way. I had to pull out a bit and back in, waiting for the lubrication to help her tight little pleasure center accept my raging hard cock.

"Oh fuck, yes" she cried "give it to me!"

Now that things were a bit easier, I pulled back, and pushed into her again, I began to increase my pace and strength of my thrusts. She moaned each time I entered her, as did I, with her tightness, it wasn't going to take long.

"Oh fuck, I am cumming again!' she cried, and her pussy erupted onto my cock, her vagina muscles clamped down and actually pushed my cock completely out of her. Her stream of cum blasted out and hit me in the stomach, I gave her a split second to finish and rammed my cock back into her forcefully opening her cunt back up again. Shoving through the contracted muscles, she squealed again, "Yes! Fuck yes!"

I lasted a few more pumps in this tight environment and I was ready with my own orgasm. My cock swelled inside her and she felt it "Please" she begged, "pull out and cum all over my pussy!"

I pulled my cock out and immediately began coating her little pink lips with my hot seed, the forceful explosions sending me reeling into my own ecstasy as my balls emptied on this little slut's cunt, stream after stream effectively covering her pussy completely.

I sat back onto the bed, spent, just as the door opened. To my own surprise, Ann stood right in the doorway. "Don't you move a fucking muscle you little slut!" she directed at Alison.

I watched as Ann crossed the bedroom, still looking ravishing and proper in her dress and heels, she lowered her head to Alison's now well fucked cunt, and began licking my seed off her pussy lips. This must have been Ann's 'one condition' Alison had mentioned.

I don't know who moaned louder, me or Alison, but my cock was stiffening at the sight in front of me. Here was my girl Ann, licking and sucking my seed from this little young sexpot's first fucked honey hole.

When Ann had cleaned Alison off to her satisfaction, she stood up and dropped her dress to the floor, as I expected, she had nothing on underneath...now totally nude, and with a mouthful of my cum, she laid on top of Alison and began kissing her passionately. I watched them for a moment, kissing, sharing my seed, their breasts pressed against one another, hands roaming, my cock was now dripping more precum, ready to go again.

I stood up and entered Ann from behind as she made out with Alison, I began slowing fucking her wet pussy. She felt warm, and wonderful as my cock began to fill her over and over again. Grabbing her hips, I picked up my pace, she began to moan into Alison's mouth. I knew she was close, her pussy suddenly clamped down on my cock, and she shuttered in Alison's grasp. She coated my cock still buried inside her. As her orgasm subsided, I rapidly pulled out of Ann, and stabbed Alison's cunt with my spear. She squealed at the feeling of suddenly begin filled again. The ridges of my cock creating intense friction against the ultra tight walls of her no longer virgin pussy, I pumped in and out of her a few times, and then pulled out and slammed into Ann's fuck hole. She grunted hard, and pushed back on me, wanting me to stay, but I pulled out again and back into Alison.

The feeling of fucking both girls at the same time was too much, and my orgasm neared quickly. As I pumped deeply into Alison, my cock throbbed and I pulled out, spraying my hot load up onto Ann's back and ass. Stream after stream forcefully exploded over her sweaty skin. She moaned with delight knowing I was in complete ecstasy. I collapsed on the bed next to them, as Alison rolled Ann over and turned around on top of her, both girls now tasting each other's sex.

Watching this was such a sight! My Ann, making this tight little 18 year old cum again and again, as Alison did the same for her. Their moans were getting more intense together. It seemed that moments later, they both came together, squirting, and coating each others faces in their love juices. Both girls then looked at me, sitting at the head of the bed, with my semi hard cock, and began to crawl over to me.

With Ann on one side and Alison on the other, they both began licking my cock together. Alternating to my balls and sucking down the length. Both women were skilled at giving head, and with both of them working their craft, I could have cum in seconds, but after the first two rounds, I was content to enjoy this feeling for a while.

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