Holly Has a Surprise or Two

Like all my stories, this one is true. I welcome all comments and I hope you enjoy!

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The title of the post was "Single mom needing a FWB, not too sure about the benefits." This made me think that she was most likely not a slut and that she would be somewhat of a challenge. I like challenges.

I sent her a nice greeting telling her a little about my situation being married forever and not being intimate with the wife for a very long time. I told her that I would be happy to be her friend without benefits and maybe even help guide her through the maze of creeps and weirdos out there. I told her that when she was done weeding through all the replies I would be waiting for her reply to me.

Her reply to me was, "You sound the most sane of all the responses I got, but you sound kind of cocky." To which I replied, "You could also call it self confidence."

I found out that she is a few years younger than I am, she just went through an ugly divorce and had not been with a man since.

It was obvious that she was out of her comfort zone and a little scared about meeting a complete stranger for sex. I was a little nervous too, and that's a good thing.

We emailed back and forth for about a month. I learned that she was living with her mom while trying to buy a house.

She also had a new job that was full time plus, and she had full custody of her son. She made it very clear that she really didn't have much time to play, she was hoping things would settle down once she got moved and was on her own.

Finally, we were able to set a time to meet. It was a Tuesday, she had taken the day off to sign papers for her new home and we were to meet for lunch afterward. By this time we had exchanged numbers and were used to texting each other about once a day. In my mind we were pretty comfortable with each other as I slowly learned she had a good sense of humor.

About an hour before we were supposed to meet I was at my bookkeepers signing checks when I got a text from Holly saying, "I just got home and my car is making an awful banging noise, I am afraid to drive it so we will have to postpone our meeting." I reminded her that I know quite a bit about cars and asked her if I could come over and take a look at it. She was hesitant as she was staying with her mom at her condo and her mom was home that day. I finally convinced her that there was nothing wrong with a guy friend coming over to look at her car.

She texted me the address saying she would meet me in the parking lot and to look for a black Nissan with the hood up. Arriving exactly when I said I would I pulled up and parked next to her car. As she quickly got out and walked over to my truck it hit me that she looked strikingly familiar to the actress Glenn Close when she was younger. Medium blond hair with those bright blue eyes got my attention to say the least.

Taking all of her in, I smiled and got out of my truck. Standing next to her I noticed that she is on the tall side.

I glanced at her feet and took note that she was wearing flats. Instinctively she says to me, "I wanted to dress nicer for our first meeting but I wasn't planning on my car having problems." I reply, "You look great, let's start this thing up so I can hear the noise you were talkng about."

She starts the car and right away it is obvious that the problem is with the serpentine belt tension. Her car was fairly new and in short order we contacted the dealer where she purchased it. Turns out that this issue would be covered by warranty. At my suggestion we made a plan for me to follow her to the dealer so she could drop off the car and then we would go to lunch as planned. Being a true girl she says, "Before we go I need to go change my clothes, can you wait here for a few minutes?"

"I will wait for as long as it takes."

She gives me a nod and heads toward her mom's condo.

As she returns about 15 minutes later I am liking what I see and glad I waited. She is now wearing heels, tight fitting slacks that show off her plump ass, a sheer blouse and a buttoned down sweater. It's a little nippy out and I am hoping to get a peek at hers if that sweater opens up a bit. Funny thing is that at this point I am not really turned on by her as she is really playing it cool.

I follow her to the car dealer and enjoy the view as I watch her walk in and then back out to get in my truck. As she gets in my truck she smiles and thanks me for being there as she would have had no idea that her car repair would be covered by warranty. I took her to a nice place for a "business" lunch. We chatted about all kinds of things. She opened up a little bit and shared that her ex was verbally abusive to her and her son, that is why she divorced him and got full custody of her boy. I told her some of my story and she seemed to understand and be ok with the fact that I am married.

After lunch I drove her back to her mom's condo. I was not expecting a kiss or anything at all and I didn't get one.

I intentionally backed into a parking space so I would be able to watch her walk away as she left my truck. She thanked me for lunch and the help with her car. Her last words were, "I want to gather my thoughts and I will send you an email tomorrow." Smiling I replied, "I will look forward to that." Burned into my brain is the view of her backside as she walked away . . . . . . . I honestly thought I would never see her again.

I drove back to my office thinking about this beautiful blonde, she was not very flirty at all during our lunch. I decided it was good to meet her even if it was only to help her with her car problem. I wondered if I should have been more aggressive, but given her past I think not.

I sent her a text later that evening saying that I enjoyed lunch and the view during lunch was very nice too. I didn't get a peek but I could tell she had ample breasts filling her sweater. She sent me back a text saying she also enjoyed our lunch.

The next day I was really busy and was not really thinking about her much when her email came in. I opened it and was not surprised at what I read. She basically said that she was not sure if she should see me again and that she may have acted too hastily when she put the ad online. She apologized for misleading me if that was the case. She went on to say that she was just too busy with her new job and parenting obligations to have any time to play. She said she thought I was nice and sweet and hoped I would find what I needed.

What I needed was to get laid!

I sent her a "nice and sweet" reply saying that I understood and she did not have to be sorry for anything.

I told her I was glad she got her car fixed and wished her the best with her new life and new job. I am sure it was just what she expected from a nice guy.

For the next few days I thought about Holly a lot. I thought how it might feel to kiss her full lips, I wondered what she was hiding under that sweater, but mostly I wondered what it would feel like to squeeze her plump ass while I buried my cock in her pussy.

On the third day of being disappointed with the fact that I blew my chance with her it occurred to me that my approach might be all wrong. The sweet, nice guy that I really am came through to her loud and clear with seemingly no effect. In a moment of clarity I decided to try the exact opposite tact and go all in with my inner most naughty man I could be.

I was driving when this came into my mind so I pulled over to compose the following text.

Hey Sexy Lady, I have been thinking about you a lot and it hit me that you need to meet my inner perv. The really naughty and nasty guy that wants to have his way with you. This guy knows that deep down inside you have an inner slut that wants out too!

We can be secret lovers and each others fuck toy, we can let it all out and be as nasty as we want to be. You know we need it.

Right away I got back, "YES!!"

I was a little surprised at her response.

My reply, "Yes what?"

"Yes I want to be your slut, I want to be nasty and I want you to bang the shit out of me!"

"Good girl, Can you meet me after work today?"

"Yes!"

"Good, I would like you to get a room at a nice hotel by the airport and order a nice bottle of red wine for us to share. Once you have all the details let me know what time to be there."

"Ok, I am going right after work. I can't wait as I need it bad!"

"It will be worth the wait and I will cover the cost of everything."

The rest of the day went by agonizingly slow for me. Finally, I got a text from her saying she was in the room and was going to take a shower. She gave me the details and I told her I would be there in about a half an hour.

I was a little bit nervous as I knocked on the door of the suite. She answered wearing one of those white robes supplied by the hotel.

"Hello Mr Naughty, welcome to my house of sin. Would you like a glass of wine?"

"That is exactly why I am here, to taste the wine."

She smiled big and I followed her in thinking to myself how much this room must cost, it was very nicely appointed with a sitting area and a separate bedroom sporting a king bed. She motioned to a chair so I took her hint and had a seat. She had the wine poured and set a glass in front of me and as she did got on her knees and removed my shoes. Her robe was too tight to get a view of her tits but I could already tell I would not be disappointed.

She sat across from me as we sipped our wine. We were silent for what seemed like a long time. I broke the silence.

"You come here often?"

We both just starting laughing really hard! A good start.

"This place is really nice, thank you for setting this up."

"You are very welcome, I feel like a call girl."

"Is that bad?"

"Not at all, no, not at all."

"How else do you feel?"

"I feel like a slut and I like it!"

She got up and walked slowly over to the window. I watched her every move as she set her glass down and untied her robe while facing away from me looking out the window.

"I am really liking the view from here, how is it out the window?"

"The view here is nice and yours is about to get better."

She let the robe fall to the floor and just stood there facing away from me. She is completely nude, I just stared as my cock was now straining to be let free. Her back side is an ass man's treasure.

She turns around and walks slowly towards me. My eyes were drawn to her nice sized tits but even more to her nipples.

Her nipples were very large, about as big around as my finger with hardly any areola at all. As she gets right in front of me I am staring at her clean shaven pussy.

"You have a rockin' body Ms. Holly."

"Well let's start this rockin' party you and me."

I set my glass down and get to my feet, I put my hands on her well formed hips and go in for a kiss. Very slowly I kiss her and just when I realize I am rock hard she reaches down, grabs my cock and starts rubbing it from the outside of my jeans.

She stops to unbutton my shirt and while she is doing that I undo my belt and drop my pants. Instantly she reaches inside my underwear and continues to stroke my dick.

She coos, "I am so happy you have a big cock, my husband was small and he never made me happy."

"My plan is to make you very happy."

I take her hand and lead her to the bedroom, when we get there the sheets are pulled back so I turn her around and motion for her to lay down and scoot back on the bed. Standing there with her laying before me I gently push her knees apart and I see that her vulva is very swollen. So swollen that her pussy lips are not visible and all I can see is a deep slit. I laid down next to her and we kissed some more as my hands roamed her body. I got around to her pussy and rubbed my middle finger along her slit, as soon as I pushed in just a bit I found her hot and extremely wet.

"Somebody else is turned on I see."

"It's been a long time and I need your cock bad."

"You will get it and get it good."

I got on my knees between her legs and spread her wide while parting her lips with the bulging head of my cock. She was very wet and very slick. I pushed my member in very slowly and I could feel her clench down on me. Damn it felt good! She moaned as if to beg for more so I pushed all the way till my balls bottomed out on her plump ass. Starting slow we got into a very good rhythm, she wrapped her legs around me as if to try and push me deeper into her soaking wet pussy. Her juices made it very slippery . . . . . .no lube needed here.

After a few minutes I stopped and slowly pulled out as I wanted to taste her. I love going down on a freshly fucked pussy, to see and suck on those swollen lips. As I pulled out she whimpered as if to complain.

"Don't worry, there is plenty more for you, I just want to taste your nectar."

"I hope you like what you find."

I found her clit and was surprised how large it was compared to the size of her inner labia. I sucked on it for a few moments and she started bucking as her first orgasm came quick. The whole time she was whimpering, it almost sounded like she was crying.

Happy that she came for me I crawled back on top of her and buried my cock back into the wettest pussy I have ever experienced.

"Go slow naughty man, I am very sensitive right now!"

"I like the sound of that you little slut, I know you want more."

"Yes I do, fuck me till I cum again!"

Hearing her say those words almost made me cum, but I was able to hold off as I fucked her very slowly.

I looked in her eyes and she had what looked like tears.

"Are you ok?"

"Oh yes, just keep banging me Baby."

She again wrapped her legs around me and it was obvious she wanted me to drill her deep.

"That's it right there!, don't stop!, Keep hitting me right there!"

"You like that you naughty little slut?"

"Yes yes yes, fuck me harder please!"

Now I am pounding her and working up a quite a sweat. She starts crying out in pleasure and she is sounding like she is actually crying. I look and see tears on her face and not sure what to do so I stop moving for a second.

Just as I am about to say something she says, "Give it to me!, I want more!"

I get back to it wondering how long I can keep this up. I feel like I am almost there when all of a sudden she starts bucking wildly and panting as if trying to catch her breath.

I can only describe what happened next as a shocking surprise to both of us. I am pounding away as hard as I can and she stops panting.

"Oh my God, Oh my God!" She tilts her head up towards her tummy and drenches us both! Hot warm liquid flows all over my cock and balls, soaking us and the bed! We were both shocked and just lay there as she came down from her high.

She catches her breath. "What the hell just happened?"

"I think you gushed all over."

""I feel like I wet the bed."

"I think you just squirted. You have never done that before?"

"Never, I am sorry."

"Don't be sorry, that is really hot."

"Did you cum too?"

"No, I was really close."

"I am sorry, I don't think I can take anymore of your cock in my pussy."

We laid in silence and cuddled for awhile. I think we were absorbing what just happened. It was the first time for both of us.

She lifts up and rolls over getting on all fours.

"It's your turn now, I want you to cum in my ass."

"That will be my pleasure."

I reach down and spread some of her juices around her ass and rub some on my cock till I am back at full attention.

Being very gentle at first, I push my dick gently into her ass and to my delight she is able to take it all like a champ.

Just seeing my cock disappear into her beautiful ass was almost enough to get me off instantly.

"Does that feel good to fuck your slut in the ass?"

"Yes it does you naughty little slut, I am going to fill you up."

"I want it. Cum in my ass!"

In very short order I went over the edge, I filled her ass with my cum as I came really hard. It felt so good to shoot my wad in her ass. I just stood there in a daze as I realized what just took place.

We took our time getting up and kinda joked about the big mess on the bed.

We were both sweaty and tired so we took turns taking showers as our little rendezvous had lasted for over two hours.

After getting dressed we had one last kiss to say goodbye. She left ahead of me so I watched her big round ass as she made her way down the hallway to the elevator.

When I got to my car I sent her a text telling I liked what I saw walking down the hallway. I got back.

"It's a little uncomfortable to walk right now."

"You are very welcome you little slut."

"Thank you Sir."