MILF Huntin'

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Giving a divorcee her first orgasm.
2.1k words
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Part 1 of the 2 part series

Updated 09/22/2022
Created 08/07/2003
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I could hardly believe my luck!! The daughter was just as hot as her mom!!

Oh wait… maybe I should tell you a little about the mom first. I met this MILF at a bar in town, famous for its great karaoke. I fancy myself a singer, so I go there every once in a while, to show my talent.

I’d never seen her before, and believe me, I would have known her if I had. She was definitely not the type of image that escapes your mind easily. She was wearing a summer dress that fell just below her perfectly shaped ass. Around 5’7”, she had raven hair and a pair of deep, green bedroom eyes, which demanded attention. She was gorgeous, kind of a Brooke Burke look-a-like. Venuzuelan looking with perfect breasts and a body that was in shape but soft and feminine looking.

All eyes were on her and her girlfriends as they entered the room. The men were staring, the women were staring as well… but most of them were staring at their men for staring at her.

Girls night out I guess. It seems as though they all started a little early having fun,
because they were definitely inebriated but not obnoxiously drunk. Luckily for me, it was my turn to sing as they were finding a table. They announced my name, the applause began. Since I’m a regular there, they know and love me. Just as the girls were sitting at the table, which happened to be closest to the stage, I caught the Brazilian woman's eye as I was going up.

I could tell from the look on their faces that they were thinking “Oh… he must be really good!!”

And I winked at her as my song began, her friends caught that and started giving her a hard time, but as I began singing my song, “Lately” by Stevie Wonder in the style of Jodeci, they all stopped and listened.

I looked deep into her eyes as I began to sing, I kinda had the feeling that she could relate to that song, as her eyes were becoming slightly misty. I could feel her relaxing and relating.

She turned in her chair to face me and as she did so, I caught a flash of sheer white panty. I almost lost my composure which is unusual for me, but I kept on singing. I think she realized what she had done though, and figured she’d have some fun with it. The stage is only about a foot high off the floor, so she turned her chair to face me and put her feet up on the stage, with her legs together. From where she was sitting, I was the only one that could see up her skirt to the top of her panties. She was looking right at me while I was singing, so were most other women, but none of them looked like her. The hardest (I mean)…difficult thing about what she was doing was that since everyone was looking, I obviously couldn’t stare right up her skirt and she knew that I think so she was totally having fun with it.

Now I have great peripheral vision so I could still see without looking. About halfway through the song, she turned her waist around to get her beer, which inadvertently opened her legs wide enough for me to see that she was wearing a thong. I looked over at one of my friends who realized what was going on and was mouthing “Daaaaaaaaammmmmn!!!” to me.

Then it hit me… as my song was drawing to a close I dropped to one knee, held her hand and seranded her, which not only made her swoon a little, but got me closer to seeing right up her skirt without making it look TOO obvious to the audience. Her friends were all hooting and hollering behind her when I was done…. I kissed the hand I was holding and then got bold and blew some cold air between her legs with my mouth, before I got up. As I got up and by her ear.

She shivered and said “Ohhhh… you’re a bad boy aren’t you?”

“Ohhh baby” I replied. “Are you gonna spank me?”

And started to walk back to my seat, as I was going by Whack! She playfully hit my butt… her friends lost it, laughing uncontrollably.

“Yeah… I know, I know” I reported to the bar. “I’m a very bad boy!”

Everyone got a chuckle out of that.

One of her friends came over to me soon after and asked me if I knew a certain song, and then invited me to their table to look at their book. There was now a chair right next to the MILF.

“Hi G, I’m Tammy, VERY nice to meet you.”

“Pleasure was all mine.. trust me.” I replied with a wink. She looked at me with a knowing, guilty smile, then she introduced me to her friends and I got to know her.

During our conversation, I found out that she was just very recently divorced. She and her friends were out celebrating. Her ex-husband cheated on her on numerous occasions during his business trips. Apparently one of the girls he was cheating on her with, found out he was married, after finding his wedding band in the hotel phone book, whie looking for somewhere to order a pizza. He was in the bathroom at the time, so she grabbed his cell phone, called home and told her EVERYTHING!!!! She then got dressed, knocked on the door left the phone outside, and told him.

“You’ve got a phone call!” and left.

As soon as Tammy’s husband said, “Hello”

Tammy said, “I want a divorce!” and hung up.

They were high school sweethearts and got married right out of high school, as soon as she turned 18. They have one daughter together and he was the only guy she had ever been with. I also found out during their whole time together she had never cum. She never had an orgasm with him either. I got her to admit she masturbated, so she knew what one felt like. He never even went down her. Sex for them was over when he came and that didn’t take that long. He was very controlling and never let her go anywhere, so this was her first night out and away so she could have fun. Her daughter was old enough to do her own thing, so she never had to worry about babysitters, etc.

I found this all very interesting, especially the parts about her never having cum before. I consider myself an expert cunnilinguist. I've studied different techniques on my own. My entire goal when I’m with a woman is to give her so many orgasm so intense and make her cum so much that she faints. If I don’t do that, then I haven’t “done my job.” It’s funny, but most times, I still have my clothes on and she’s completely naked and squirming under my mouth. I learned to take at least my shirt off, because I love to give G spot orgasms, which as you may or may not know, get VERY messy.

By the way, I’m telling her all this, and she (and her friends} attentively listen. I tell them that all women are capable of female ejaculation, and only one of them had actually experienced it. All the other girls there were telling her she was lying, because it only happens in the porn movies.

“I can prove it. I have proven any woman is capable of it many times” I say.

“Really?” her hand going to my leg.

“Ok, I guess there’s only one way to prove it.”

“Ohhhh.. I see where this is going!!!” They all laugh.

“Ok, I’ll make you a deal, just so you know I’m not full of it. Let’s all go to someone’s house and I’ll prove it. You will all be there so you won’t have to worry about anything happening that you don’t want to happen.”

I could tell they were still hesitant.

“Ok… how about this. Unless you ask me to take them off, my pants will stay on. Let me just take my shirt off, cause it’s going to get really messy.

“I’m game” Tammy says out of the blue.

I didn’t expect that to work, but hey, at least I’ll get the hottest one of them all.

“My daughter is over at a friends house so she shouldn’t be home till morning probably. I've got nothing to lose and if he's telling the truth.... A LOT to gain. Let’s go.”

“I’ll follow you in my car then.”

“Yeah, I’ll come with too, says her friend Betty, a voluptuous redhead, who had just enough to drink so that she didn’t really care what happened at this point Was this really happening? Then her friends Susan and Tonya, both blondes said “Ok… if you’re going too, I don’t wanna miss this. Just to watch though.”

Tonya was a strawberry blonde kinda skinny not much up top but she was looking really hot in her skin tight outfit.

Susan was a stereotypical blonde, valley girl. You could tell she was head cheerleader at one time. She was married.

I said bye to my friends and told them I’d fill them in later, then Tammy and I walked out hand in hand.

“God, I feel sooo wild and free right now. I have never done anything like this before.” I hope you can back your talk up.”

As we got to her Lexus GX SUV, in the parking lot, I walked over to open her door for her. It was just habit for me, but of course I had ulterior motives.

“Oh my god, no one has EVER done that for me before!” she exclaimed.

Then pulled me against her with her back towards the SUV and began kissing me hungrily, dry humping me passionately, her hands roaming all over my back and down to my ass, pulling me closer into her so she could feel my growing erection.

She moaned into my mouth as she felt another man’s cock against her for the first time. She pulled away panting heavily and I continued opening the door for her as she got into the driver’s seat. This time her panties were in full display in front of me this time, and I took the opportunity to plant a very wet kiss on her inner thigh, very close to her panties, she automatically spread her legs slightly, and I let my tongue travel in towards her lips slowly. My tongue traveled the length of her panties as she shuddered in ecstasy. I could smell and taste how wet and excited she was.

“Oh… you work fast!” I hear the giggles of her friends behind me. I began to pull away, but Tammy held my head so I could not move…

“Ay Dios mio… I’m getting close already… don’t stop!” she says breathlessly.

“Really? Seriously? Holy shit.. he IS good!! Right out in the parking lot too?”

I began put suction over her clit and began her clit right through the panties in and up and down motion. Her legs began to shake as she came. I held on to her clit for dear life as she continued orgasming and spasming. I could tell she was trying to stay quiet but it was her first real orgasm, and she was too far gone to care. I could hear her friends gasping behind us as she came down from her high.

A few minutes later, she said “Wow! I had no idea it could be that good! I've been thinking about your mouth down there since all this talk started."

“And you still have your panties on!” A voice from behind us said jovially.

“Oh wow…. Ok… get in. I’m taking you home. I can’t wait to see what else you can do!”

“Yeah.. we’re definitely going to your place now!” her friends say. If I didn't know you I would think you were faking. He really made you cum THAT fast."

"Well actually she just had an orgasm... she hasn't cum.... yet." I say.

"What do you mean?" Betty asks.

"There is a HUGE difference between an orgasm and cumming."

"There is?" Susan asks

"What do you mean? THat was pretty damn intense!" Tammy says

"Oh... that was nothing! Believe me, when I find your G spot and make you cum... you will feel the difference"

"Oh my God... let's go.. I think I'm a believer already, but seeing is believing" Tammy interjects. “You have to drive though G, I can hardly feel my legs right now!”

{to be continued}

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