Debbie's Night She'll Never Forget

To understand this story better you need to know Debbie she was a divorced mother of two who was used to living the posh life of a kept executive's wife until he found greener pastures with his young secretary. So, she was on her own for the first time living comfortable but not the lifestyle she had grown accustomed to so she was reduced to working for a school where she told me she was ogled and hit on by every low life bus driver, janitor teacher you name it so she was looking to date a normal person hence we met so much for normal.

She was in her mid-forties about 5'-8" tall 145lbs nice round ass pretty tight body but greatest asset was her 40DD tits glorious melons with nice pink nipples that got erect very easily even when talking dirty to her they would perk right up she had the hairiest bush I had seen on a woman nice thick lush hair, but she was seriously lacking in sexual imagination and creativity. I honestly think she learned how to give a blowjob by watch some lousy porn. She never thought outside of the box and relied on everything her mother told her about sex both good and bad mostly bad.

She wouldn't swallow or allow me to cum in her mouth she was not into any experimentation but told me she had deep down curiosities about many things but, do to her "sexual hang ups" she said it would take something or someone special to break through all of the taboos she was so wrongly taught in her younger years. Basically, sex was for procreation and to satisfy your husband to keep him from having a wondering eye.

All I could say to her was you, poor lady your wasting valuable time. We dated for some time and had the usual petting and not much more that some deep tongue kissing which she wasn't bad I must admit. Being the boob man that I am I was instantly attracted to her shapely 42D melons which she had no problem teasing me with even from the first time we met.

In the previous story I broke the ice with her in a most unusual way by allowing her to tie me to the bed so she would feel like she was in total control and it was a sign of trust but it didn't take me long to figure her out and the key to opening her legs and gaining access to her pussy was simply let her think she was in control but the entire time she was playing right into my hands. Her intent that night when she came over was to just kiss and allow me to play wither big tits but the end result was a wild night of fucking

Well after dating for some time and releasing her inner wild side exposing her to many firsts. We started with her first sex toy, here was a woman who had never seen a vibrator in person let alone held one or used one. Oh, you poor baby I said lets fix that. So, we set off on a sex adventure one night right after work Debbie arrived at my place and excused herself to go use the bathroom she had to change for our date she had on a nice blouse and a short skirt looking classy yet sexy. I smiles and said wow you look very nice, she thanked me gave me a kiss and said I wanted to look nice for our date, now shall we go. I returned her smile and kiss and took her hand leading her to by hand to my truck.

I knew of this classier not at all seedy sex shop up north so there was no chance anyone would recognize her which like a lot of women I suspect was the biggest obstacle preventing her from never going to such a place. We went in and there was a mix of couples and single patrons milling about and we went over and looked at vibrators a very nice young salesgirl who looked like your typical college coed more than a salesperson in a sex emporium came over and offered her assistance.

She smiled at Debbie and asked first time?

Debbie instantly turned red with embarrassment and the girl put her hand on top of hers and said no reason to be embarrassed everyone has to have a first time it's nice that your boyfriend or is it husband came along with you.

Debbie said he's the expert and the girl laughed and said why don't you guys come with me and she lead us to a private room towards the back not a place to have sex but a place to have some privacy when getting personal service actually a very smart business move on this place as it most definitely worked on Debbie who now totally opened up to the girl who brought back an armful of devices from the show case, she had Debbie touch and hold them and instructed her on how to use them etc.

The girl would not actually demonstrate but do things like lay a vibrator against her crotch and talk about insertion, clitoral stimulation G spot orgasms and then she asked her point blank, does your boyfriend satisfy you orally she asked. Debbie was embarrassed and blushed a bit she looked at me and said he's fantastic, I just gave her a smile and said thanks babe. The girl said you like how it feels when he stimulates your clitoris so how do you think this would feel and she turned on a small vibe and gently placed it on her wrist, Debbie looked curiously but didn't give much of a reaction she said ok I guess, the girl looked over her shoulder and softly whispered I'm not supposed to do this and told her press it against your panties but DON'T! put in it please, she handed it do Debbie who looked a little confused and I just took her hand lifted her skirt and guided it to the front of her panties and pressed it against her pubic area approximately in the area of her pussy and she had a facial expression that showed she liked what she was feeling the girl softly whispered move it around until you find your clit and looked at me and said be prepared to hang on to her and no sooner were the words out of her mouth when Debbie found it and it was all she could do from letting out a loud moan she closed her eyes and put her head back and she said oh my! this feels great, the sales girl said see and said ok but within seconds Debbie you could see by the expression on her face that something was happening she was cumming but had the presence of mind to stop and she took the vibe out from between her legs and put it on the table.

She smiled and said I want one of those please. She held my hand and without trying to be too obvious placed my hand on her soaked through panties. I looked at her and mouth the words did you cum and she leaned in and whispered almost. The girl showed us a variety of dongs vibrators eggs you name it. She brought out this monster rubber cock and said here you go Debbie think you can handle this big boy she laughed, so now miss prissy grabbed the shaft of the big cock and pretended to stroke it and then said something completely out of character saying can I check it to see how it fits first before he buys it and pretended like she was going to take it under the table and put it in her pussy, unknown to our sales girl was soaking wet with her juices.

The girl laughed and said If I were allowed to let you try it I would and if you could take the whole thing it would be on the house. I laughed and said would she get her picture taken and be up on the wall of fame, we all laughed and Debbie looked at me and said oh now you would just love that wouldn't you, I responded with a smile yup sure would the girl also laughed and said hey I'd love to see that myself. We all chuckled but Debbie looked at me saying well it's your treat so it's up to you babe. I said sure why not, the two laughed Debbie said well it might take some time but I'll give it the old college try.

Our girl laughed and said ok deal I'll arrange a private visit for that. With that she wrote up all of the stuff Debbie wanted as they chatted, I told them I wanted to take a quick look around and would be right with them. The two headed off to the front counter and the girl pulled new items out and placed them in a sharp looking shopping bag like you would see in any higher end department store and threw in a bunch of free samples of lubes and lotions and assorted colored condoms. I had spotted this red pvc bustier outfit on this mannequin when I was walking in, I made my way to it and there was another girl straightening up clothing and shoe boxes and I approached her and see that tall redhead at the counter.

She looked up and said yes and asked your wife I said no girlfriend what size in that, pointing to the outfit do you think she would take, I want to surprise her this weekend oh how sweet she replied and said oh that's easy they have a stretch back so they fit very well but here this would fit her perfectly and handed me a box and said wait you need the matching stockings I was like man another option just like the car dealers she threw in a package containing the thigh high stockings and asked shoes or boots? I said not this trip.

So, she walked the box up to the register with me and just pointed the label towards the other girl, so Debbie couldn't see it. I pulled out my Amex card and handed it to the girl who was helping us Debbie kept asking so what did you buy and I said a surprise she said oh come on please show me I said nope with that our new friend proceeded to tape the box up and said nope sorry Debbie you're just gonna have to wait until he decides to show you and smiled and said but I know you'll love it and Debbie just gave her best fake pout. We took or purchases and headed back out to my truck, the girls smiled and said see you soon guys it was fun yeah, I can't wait to get the bill from Amex....lol.

We got in and drove to a nearby diner to grab a bite the entire time she talked about the experience and how exciting it was to be doing something that was in her world so taboo I said in your old world maybe but not in your new world baby, she smiled squeezed my hand and said my new world and gave me a kiss. We ordered food and we were waiting for our meal when she excused herself to go to the lady's room, when she returned, she scooted up next to me rather than sit across from me and took my hand and placed something in it. I glanced down to see her soaked panties in my hand she smiled and whispered put them in your pocket which I promptly did, and I took the liberty to take advantage of our closeness and put my hand up under her skirt probing around until I found her wet pussy.

She unzipped my jeans and pulled my cock out and began stroking it She casually talked about our little sex adventure and how much fun it was going to be and she couldn't wait until we got home (meaning my house) try everything I was gently and slowly fingering her pussy when she said do you have any sick days you're not looking too good I think you should stay home tomorrow. Who am I to say no to the woman whose pussy I'm fingering I said sure just need to call out sick? She said give me your phone, I reached for it with my left hand and handed it to her and she said what's your bosses name Bo right I said yup as I probed her snatch getting wetter by the minute, she stroked me faster and faster with the obvious intent of making me cum right there at the table every once in a while smiling wickedly at me whispering are you ready baby? Before I could utter a word, I felt my cock explode in her hand. She casually whipped her hand and my cock clean with a cloth napkin. I was both relieved and somewhat in shock as no woman had ever jerked me off in like this before and was totally composed the entire time.

When he answered she said Bo this is Debbie we haven't met yet but I'm Bob's girlfriend I could hear his voice but not make out what he was saying, she played her part perfectly and said Bo he's really not feeling well I wanted to take him to the hospital but he refused so I made him go lay down but he has a very high fever bla, bla, bla, she was very convincing and just said to him ok I'll take good care of him I promise he should be back on Monday but if not he'll let you know.

I had to be a devil and finger her harder and faster in an effort to get her to at least stutter, but she was great and never skipped a beat. She put the phone down on the table and said now I need to take care of you the entire weekend you heard me. I said yes nurse I'm feeling pretty damn good right about now though fingering her wet cunt. She smiled and said honey you'll have to continue this on the ride home our dinner's here, I was never so unhappy to see a waiter.

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