Title: New Years Eve Surprise



"Hey Roger who is that over there" he asked. Roger asked Bob who he was referring to and Bob pointed her out. After learning her name and getting the details on her Bob headed over to the tall full figured woman wearing a velvety long gown.

It was New Years Eve and Bob didn't have a date, but went to the benefit anyways. He figured there had to be a few women like himself and without dates looking to hook up.

Bob charmed the panties off the woman he saw although they hadn't hooked up for the night. It was there intention to catch up later on and meet upstairs in her room so they could spend a wild intimate night together.

Her name was Romaine, she was the executive director of one of the charities hosting the event and Bob was on a mission... she happened to be his goal. She was alone since she was its host and she felt she needed that added attention when the evening came to a close after midnight.

Looking forward to getting together with the charismatic younger man Romaine at 36 saw no problem being with a young self-assured handsome guy like Bob Pellet. He already showed he liked her. They danced together consummating the fact each felt the other was adorable. Both laughed with one another when they had time to spend it together and she offered him her room key so he could head upstairs.

Picking up a couple of bottles of champagne on his way up, he already had a few too many as it was and displayed significant signs he was well past the point of being sober enough that he could be charming and swipe her panties off respectively. Nevertheless he arrived up at the eight floor unharmed even though he bumped into walls, tripped over his own feet and managed to keep himself afloat along the way. Bob was still excited about having sex with the stately and gorgeous Romaine.

Problem was when he arrived at the room supposedly reserved by her, he looked at the card which read 835 and stood in front of a door reading 836. "835... this must be her room" he told himself in a drunken slur. "Well I guess I'll sit here until she comes up and when she knocks... I'll let her in. We'll have some great fun.

Sitting on the couch in room 836 he wondered where she was. Oddly he never thought about the fact of how he could get into 836 when the card said 835, but he was too drunk anyways to realize it in the first place and Bob eventually grew tired and walked to the bedroom.

Lying down he kicked off his shoes as he lay on his back thinking how beautiful Romaine was that night. Too drunk to recall details he remembered three things. "She's tall, she's got big boobs and she's a hot looking big woman! Yep... a hot looking big woman with big boobs... mmmmm I can go for that" he said slurring his words.

Lying and waiting for Romaine to come he grew anxious but never upset. Slowly he took off one item after another as he removed his tuxedo jacket, his tie, cummerbund and finally his socks.

He felt pretty good but the damn bed was spinning on him and he got up to vomit. He washed his mouth out and then he gargled so he felt a little better but he heard a door close and said "It's about time. God I wanna sex her up."

The woman walked in to the bedroom and put her hair down as he lay watching her. With the same build and same features, he imagined Romaine's face and figure. Same shoulders and similar looking wide ass he smiled as he watched her from behind.

The woman had no idea anyone was in her room and started to talk aloud. She too was slurring her words laughing and joking to herself. "Man if only I hadn't gotten married I'd slip that young man up here with me and we'd... yes I would. I'd get that youngster in here with me and I'd show him what real sex..." and she started giggling.

Bob watched her walk away and smiled knowing it was Romaine. Soon he would be at it... getting it on better and harder then anything he's had in weeks. He unbuttoned his shirt and removed his slacks lying and waiting for Romaine to come back.

"Hey I'm in here" he called out.

"Honey hey baby I didn't know you were coming" the older woman said as she stumbled back to the bedroom. He could see her but she didn't really see Bob's face. "Awww that's sooooo sweet of you to come to me baby. I missed you tonight. Thank you for coming back. Hey lets make love like we did on our honey moon okay Will you make love to me like we did on our honey moon" she asked in a drunken tone of her own. "Just like last month okay" she went on to say.

"Huh what" bob asked as she collapsed on top of him. Before he could resist whoever it was on top of him and kissing him passionately. He couldn't tell if she was drunk or not. He was too so he couldn't smell alcohol on her. Her hair was long like Romaine's, her body was built like Romaine's too and she was tall and just as sexy and both were drunk and delirious. "Wow you kiss... geez god I love your lips... they are awesome" he said. "And your body... it's like... like a freakin air mattress but sexier then sexy" he told the woman who was passionately kissing him.

Neither had a clue and neither cared to much either. Sex was on the brain and he had a partner regardless. "You feel incredible tonight baby" she told him. "God I didn't realize how sexy you feel baby."

"Thanks Romaine you do too."

"Huh... what" she exclaimed. "Romaine who the hell is Romaine... Charlie" She looked up and strained to see who she was kissing. She realized she wasn't on top of her husband. "What... who the hell are you" she asked in a frightened voice.

"Uhhh who the fuck are you" he asked. You aren't Romaine even though ya sure look like her. Damn you almost look like you two could be freakin twins. She pulled away from him and hopped off the bed.

Lying on her bed with his arms behind his head and behaving as though he wasn't too worried Bob looked at the woman who had taken off her gown and was in some piece that accentuated her fuller figure nicely. With his shirt open and only wearing underwear he looked the sight.

"I'm Carol Crawford and who the heck are you young man" He told her who he was. "Well Bob whatever your last name is it's nice to have met you and kissed you but I think it's time for you to go."

"Nooo wait we were just getting started Carol. I was learning a lot form you in the short time you spent on top of me. I mean hell Carol ya got a great set of lips, a really nice body and heck who knows... if we take it easy maybe we can have a good time here tonight."

"Are you crazy" she said slurring her words.

"Yeah I'm crazy so what do ya think" gesturing her to come back to bed and snuggle with him so they could play around. Bob had a smirk on his face the whole time he tried persuading her. "Hey were both drunk I think; you sound like ya are and I know I am and I like what I see. I mean ya do have one hot nasty looking body for a woman your age and it seems as though you're as horny as I am... right Carol... right"

She stared right into his eyes listening to his 'sales pitch' and before she knew it she was climbing into bed with him. "Do ya know how old I am Bob Do you have any idea how old I am I bet ya you don't do ya

"Looking at you... hmmm... yeah stand up again will ya" Bob asked. Smiling after she got back out of bed and turned around he said "Wait, stop a second... stop right there" as he looked at her mature ass. "Yep now turn around again please... oooooh yes that's it... mmmmmm wow Carol you're one hot sexy ass woman! Yep you sure are. I'd say you're about 54... No wait sorry about that you are 52 right... am I correct But let me say this... you are one very sex 52 year old woman. Now come back in so we can have some New Years fun together. Come on..."

"How could you be so right How can you do that... guess my age like that"

Winking and smiling he replied "Because I'm good baby... I am that good Carol."

She couldn't be more delighted he guessed her age correctly. He charmed the stockings off her and she was next to him playing with him and his chest hairs before she knew it.

"You're a cutie Bob. Can I pack you away and take you home so when my husbands out of town I can use you"

"Sure... but let's see how well you do me... alright"

Carol slithered right on top of young Bob's skinny frame. As she did her fingers danced around his chest, shoulders and down over his legs. She was having more fun then Bob but Bob always loved this part... sexually arousing his partners... especially ones which were older then him.

"Oooooh you feel incredible Carol... all warm and squishy; all rolly polly too. Oooohhh smash against the bed. Squeeze your big bad curvaceous body all over me you hungry sexy babe you!"

He drove her insane speaking to her that way. He loved her plump figure making its way around his slender frame. He awakened her physically and she yearned for him to move forward on her.

"Dip your hands inside my undies... find that treasure you crave" he told her. "Find it and wield it in your hand...take hold of it! Be its master Carol! Be the master of it baby" he commanded.

"Ohhh Bob... Bob baby yes I will... I will be its master for you! Yes I want it... I want it badly Bob... ohhh so badly yes!" Carol slid her hand inside his underwear grabbed hold of his limp cock and squeezed with the greatest enthusiasm she could muster. "Fuck Bob yeah honey babe... I can't thank my lucky stars having you here with me! Thank you... thank you... ohhh yes yesss thank you honey" and she pulled his underwear down, reached down towards his cock and swallowed it inside her mouth to pleasure her unexpected guest.

"How do you like it honey huh How's that Am I doing it good enough for you baby... am I" He told her she was fine as he rested with his arms still behind his head. "Is this better" as she put her mouth back on it while it stiffened more and more. Gagging off and on he became hornier at the sound of her gagging.

"Well I think the time is ripe. Let's get to the good part. Bend over Carol so I can insert myself up you alright girl"

Carol got on all fours as he mounted her from behind and Bob went in and began banging the woman to her never ending delight. Carol screamed and moaned as her flexible mature body took a wonderful enjoyable beating. Bob brought her to orgasm shortly afterwards as she shrieked and screamed for him to hold her just after she climaxed.

"Was I or did I meet all your expectations" Bob asked Carol.

"Ohhhhh Bob... Bob yes... oh god yes you did. I want you to stay here... Stay with me and we can fuck later on please. Please stay so I have someone to hold tonight... please Bob" she pleaded.

"Tell you what Carol... Let me get you're address and phone number just in case, but give me a few hours and I'll be back around say 4. I have some business to take care of right now... I'll be back okay You are incredible you know. I mean you sure know how to do a man right. Thanks Carol... thanks a lot."

Bob left and went next door. As he opened it there was shouting and screaming. Carefully he walked back and there he saw Romaine fucking some guy. Not knowing who it was he said "Thanks anyways Romaine... maybe we'll get together next week like we always do... okay"

He walked out leaving her in the lurch. Both Romaine and whoever it was she was screwing were shocked he'd even come by. He was bold and brass, but he had the balls. Regardless he went back to Carols and the two of them had sex the rest of the night.


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  • Story Details and Information
  • New Years Eve Surprise
  • Published: Dec 30, 2007
  • Author: Stoneypoint
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  • Category: Short stories
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About: "Mature woman fucks young man unexpectedly. Carol got on all fours as he mounted her from behind and Bob went in and began banging the woman to her never ending delight."

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