Jennifer’s Wise Advice – BDSM – Free Sex Story

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Editor: ShadySweet

Special thanks to ShadySweet for helping me with editing.

My Sex life was diminishing into a routine; my boyfriend seemed to be interested in everything except me. My insecurity was hitting red and I was not in my best shape. So I decided to talk straight to my best friend Jennifer, who mysteriously seemed to always have a good solution to provide, no matter what the problem was.

So we went to a cute chocolaterie downtown to enjoy a cup of Hot chocolate with a bit of Black Rum of course.

“Just fuck him,” advised Jennifer, with that look of wisdom on her face.

“Think we haven’t done it yet? Me and Ritchie have been together for more than two years now, what do you think, we are just holding hands?”

“My dear Mariah, I mean literally. If you want to start the fire in your relationship there’s only one way sure and fun that works for all men: Fuck him.”

“You mean… no, you don’t!”

“Yes,” said Jennifer with that cunning look in her eyes and the sardonic smile, giving me a few seconds to realize it; then added plainly and clearly:

“I mean that you have to fuck him with a strapon.”And sipped a bit of her chocolate.

“Are you nuts? We are talking about Ritchie, not anybody, you know him. And I have never done something like that, I don’t know what to do, I don’t even have the…”accessories”.

“That makes things even better. It will be the first time for both of you. How romantic!”

I was stunned. She continued with the style of the person who knows 100% the truth and she generously shares it.

“My dear Mariah, men, unlike women, are lust-oriented creatures, instead of Love –oriented as more sophisticated beings, like us, are.

And the real way to man’s lust and therefore (that’s how men are) to his heart goes through his anus; it can be a lot of fun!” she paused a little to enjoy my surprised expression and continued:

“What is the most erotic part of yours?”

-“I suppose my clit…?”

“Perfect! And men’s?”

-“Their dick of course.”

“Nah! Their clit too. And it is shoved in their asses. For some strange reason, mother nature hid the best tool to a man’s Orgasm where no man should ever let anyone play. It’s called the prostate and once you start massaging it…they simply lose control. And… guess what”

– “What?”

“YOU take that control”, triumphed Jennifer.

-“Well…could be… but you know I am not that kind of person, I mean I am petite, and a typical introvert I’m just 28 and he is much older than me…”

“That can make things even better. The student fucks her teacher! Wow! What a role reversal!”

-“Hey, you seem like YOU want to fuck him”

-“Nah, you are my friend, he is your man, I don’t touch. Friendship is sacred to me. It’s just that I want you to be happy. And…”

– “And?”

“One macho male less, well, makes the world a better place

-“Aaahmm so let’s suppose that I am willing to try…”

“Perfect! Join the club!”

-You mean that you have tried it?

“Hahahahah! Tried? There is no way for a man to make Love to me without getting pegged, at least for the last, hmmm, five-six years”.

-“Pegged is…”

“Yep. The technique is called pegging. And yes, when you fuck your man in the Ass you can say you peg him”.

-“Don’t you tell me that you and Alexander…”

“Alexander is my one and only lover and whenever we meet has an obligatory plug shoved in his beautiful Ass. It would be a pity -don’t you think- for such a great peach like Ass, to remain unfucked?”

-“Well…”

– “Enough talking, let’s go.”

And she took me to a woman-owned Adult toy shop that was beautifully decorated and full of strange and curious things. So we took everything and lots of lube, a Free ‘manual into pegging’, and a lot of best wishes from the cashier, and went out. Jennifer also offered me a tutoring DVD and in a couple of days I was ready. At least, theoretically.

So, Saturday night came and we went out to a nice restaurant, when I

asked Ritchie to come to my home. He was kinda stressed about his job so when we went home and started kissing and moving towards the bedroom, I said swiftly into his ear:

“Boy, you are so tensed I think that you need a massage. Lay on the bed, and close your eyes and let Val take care of you.”

-“Who is Val, Mariah?”

“It’s my alter ego. Who loves you even more than Mariah. Will you let Val take care of you?”

-“Yes, baby, yes!”

– I could see from his face that it seemed to him like another crazy girlish thought. If only he knew, what I had in stock for him. I started removing his clothes. I turned him face down in order to massage his back. I jumped on top of his ‘soon to be fucked’ Ass and started applying baby oil, (to get him used to substances applied on his body) and continued massaging him sometimes stronger, sometimes softer. But in any case, without losing control as my “tutor” had explained to me. I had the lubricant beside the baby oil, using it alternatively so he couldn’t tell the difference. Soon I noticed him rubbing his dick onto the mattress; he was already erect, good! Jennifer’s voice ringing in my mind: ‘It is important to have his logic placed aside. Don’t let him think. You don’t need that. He must feel’. And

keep him erect or semi-erect but for no reason you should let him ejaculate. If this happens then the game is lost. Men have only 5 minutes of clear thinking and those are just after Orgasm. You have to start again another time. Don’t forget to tell him that HE is your MAN, make him feel secure for his masculinity’

-” Baby, I said swiftly to his ear please stop rubbing yourself to the bed. I wouldn’t like to lose your valuable juices. I’ll take care of you pretty soon”. And by saying that I started massaging his butt cheeks. Then I laid to his side placed my tongue in his ear, seeing him shivering and whispered

-“You are my boy, my man, and I Love you so much, so much my boy, my beautiful boy”

While saying those words my hand was already circling his anus and my middle finger started pressing in. I kept talking smoothly into his ear, pressing a little more each time. Of course, my finger was each

time more lubricated. I’m not sure whether he figured out what I was up to. Maybe he knew. Maybe not. But I had to go by the plan.

Didn’t want to take any unnecessary risk.

Slowly, my finger hit the target. Got in. I felt his Ass muscles encircling it and pressing it outwards. I kept pressing firmly making slow round moves. And speaking soothingly:

-“My boy, my lover, how beautiful you are. Relax my Love, you are so tensed, let Val take care of you, I am here for you, let me take care of you”.

Saying that my finger went deep inside. Now my fist was hitting his Ass. Great! We are creating an opening. Yeah! Now let’s make this narrow path a real road. A road to happiness. I was so wet. So wet for just toying him. Started rubbing my clit on him. He was there, seemingly still, but breathing heavily without opening his eyes not for a moment. Started pressing the second one. Slowly, with round moves. Kept talking

-“My boy, Val will offer the best massage of your life. The best cure for stress. Do you like Val’s massage Ritchie? Do you?”

“Mmmm”, came a moaning from an animal hidden inside him. Great! I wanted to scream! So I became more serious. Pressed more. More lubricant, most pressing and soon I had my middle and index fingers inside the entrance of his asshole. Was quite difficult to have them both deeper inside. Kept talking.

-“Oh my boy, my lover relax, relax and let me take you to another level of joy. I am Val, I am here to serve you. Take a deep breath. Come on”. Yes! It worked. I had both fingers inside him. He unknowingly was pressing my fingers. But I kept moving them round and in, round and then out and then in again. In and out, in and out, more forcefully now. And

“Do you like it boy? Like your massage?”

-“Mmm yes.

“Do you want me to continue?”

-“Yes, yes”.

Never have I seen my Ritchie being so obedient. Jennifer rules!

I kept pushing my two fingers inside him till my fist hit his Ass, not so smoothly now. I was seriously finger – fucking him. There was no massage- cover anymore. He was moaning. Deeply. He was breathing heavily, a locomotive breathe. Somehow his lust was being transmitted to me. I was receiving his vibes. My fingers were no erotic spot. I was rubbing my clit on him from time to time but this was nothing compared to the wave of lust that was filling me. I was wet and I wanted to violate his Ass.

I started forgetting his pleasure. That man is mine. That body belongs to me. I am claiming it. It is mine. I can play with him. I can place my fingers up his Ass if I please. He will accept it. He is MINE. MINE. Now my boy, take the third one. With round moves and tons of lubricant – surely he felt that cold thing covering his small hole and spreading all around, then pressed in a third finger. Suddenly he opened his eyes and I felt like a thief caught in the act. I feared that I had blown it. But didn’t freeze. Looked at him, straight in the eyes.

Love you, my boy, you are my man my one and only lover, MY boy.” While saying that, I forced the third finger deep inside him.

-“Aaargh,” he screamed but I kept pressing. In and out. In and out till the tip, till before he would feel relieved and then in again till my fist would hit his Ass

I had no reason to hide anymore. He was there, under my spell, receiving my caresses. And, yes, I was finger- fucking him. Yes, that was my lover and mentor in many ways, a person I Love and respect and I couldn’t ever imagine placing him in that position. Such a shameful position for a strong male. Still, I was not Mariah, anymore. I was more Val, a girl, a woman who liked to play, to care and conquer. I had a plan. I was going to fuck him. And this was only the prelude. Had to continue.

I kept moving my three fingers inside him and out. And round. Sometimes I felt touching something like a button. Each time I hit it he shook and trembled. And said things like: “Yes, oooooh yeeees, yeeess, oooooh, my baby!” with a voice coming deep inside him.

Obviously, I’ve hit his G spot. All right. Now he looks happily mad, or should I say madly happy?

I have to continue. After thrusting into him for some minutes more I felt the tension around my fingers somehow relaxing. So…he was opening. Yeah! I got you, little Ritchard. Who is the boss now? After three — four more heavy, violent thrusts without serious resistance grom his side I said:” Now boy, you take a small break and I’ll get you to the next level.

-“Yes Love, yes baby.”

I slowly removed my fingers, and kissed him passionately, shoving my tongue into his mouth, making him follow mine. When I felt I had enough of his mouth, I whispered into his ear

-“Now boy don’t move I’ll be back in a moment.”

I stroked gently his hair and went under the bed where -following Jennifer’s orders- I had placed the magic box. I opened it and took out the first toy. A black butt plug. A silicone plug, made special for beginners.

This time there was no prologue. Spread his Ass cheeks and stuck my tongue in his asshole. Made it round and strong and pressed. And Pressed. Yeah! That was the sign. ‘If you can open his asshole with your tongue alone, then you can shove anything you want in him. But you have to do that progressively. Start slowly. The future is yours. He will be begging you. Begging YOU to FUCK him. Just be patient. Move swiftly’

Jennifer’s words leading me once again. My hands opened his Ass cheeks. Now I stopped for a moment to admire my work. There was my man laying on the bed, completely left to my disposal. Breathing heavily, moaning. With his Ass opened. Opened to me. I felt an impulse to shove my whole fist in him. But no. I shouldn’t even try it. Had to start with this plug which looked so large when I first saw it at the shop but now seems perfect sized for the occasion.. I started pressing it inside of him. In the beginning, it was hard to move. Had to press more. And little more but then, something happened and it got all the way in, up to the wide round tip. Seems that I took his virginity. How wonderful! So, that’s why these toys are made like this. It could have been lost in his depths.

A day before, it would be crazy to even try to touch him down there with a finger. Just touching was unimaginable.

Now, his well-lubricated and caressed Ass sucked the ‘small Anal plug’. He just sucked it. Oh, what a slut! I am in a relationship, for more than two years now, with a slut, without knowing it. Now I started pressing that round tip of it, seeing him almost unconsciously¶moving his Ass against me. Oh boy, so you want more? You like me filling your small hole? I fell to the side, although I could enjoy the view of his conquered body for hours. I spoke into his ear again,: ¶

“I’m so proud of you trusting me to massage you. You have a wonderful body, I Love you so much, I want you to let me play more with you.” All this was said while I was pressing the plug deeper and then letting it out for a second and again.

-“Yes baby I’ll do anything, anything that you want, I Love you, you are my only Love, the one I Love deeply.”

Wow, what a sensitive lover I’ve had without having realized it.

“So you’ll do anything for me?”

-“Anything baby, anything at all”

-“All right, relax now and I’ll come back to you”

I went under the bed again and opened the magic box. Now it was time for my strapon. Following Jennifer’s (God bless her) advice, I bought the most crazy looking; a small shiny purple one. One that resembles a toy and in no way a real dick. So it wouldn’t trigger his resistance. I had it ready in its straps. I stood straight, feeling so strong, so powerful strapping this purple piece of art on me. I felt like I filled the room although I was still only 5 feet tall. But I was going to fuck my boyfriend, my soon-to-be husband, the Love of life, my mentor my…

Yes I was going to do it. I hesitated for a moment but then I said that I have to complete it. Without thinking. Just feeling. And I was feeling great!

So, I touched his dick and felt that it was filled of pre – cum. It seems we were both ready and wet. Placed a large pillow under him -I wanted him to be comfortable- and gently removed the plug. For a split second, I noticed a glimpse of disappointment on his pretty face. Maybe I imagined that…Now the lube. Tons of it. On and inside his asshole and of course on my purple strapon. It shines a bit more now under the dim light of the candle ( of course I had prepared an atmosphere with candles and sticks burning).

I grabbed him from his hips. Then aimed Georgia (the idea is that I am going to hit his G – spot, so Georgia is an appropriate name for my toy) to touch his tiny hole (how rapidly it closes- incredible!) and then I had to take the right angle. ‘It is important to push to the right direction otherwise you will hurt him or you will never enter’, again Jen talking in my mind.

I pushed slowly, and grabbed him from his hips, saying

“Come on my boy, breathe deeply, it’s me, it’s only Val, have no

fear, show me how you trust me, breathe, breathe for me..”

And then it happened. It magically happened. I had the tip inside him and with a small thrust, it was all the way in. All the way in. I did it. I was top and he was bottom. I was in control. I could move faster or slower. I could go in and out. In out of HIS body. He was getting penetrated by me. A young girl, a small quite young girl is fucking this beautiful strong man. Yes, he is mine. This body belongs to me. And he will cum when I want him to. I control him. I left my whole body to fall onto him, to cover him. My hair was all around his head. My mouth was gently biting the lobe of his ear. He could hear me, breathing. I was so wet that for a moment I thought the whole strapon could somehow get inside me. But no, of course this could not happen. So. I started slowly moving in and out of him. Created pace. Left him feel my smell, my voice in his ear, my breasts on his back, the whole of me on top of him, and my small toy inside him. Stroking inside him.

Each time deeper inside and up to the tip. Then I placed him on all fours. Spanked his well fucked Ass once and took position behind him. Pressed his waist until he was at the right height. Now I was holding him firmly from his hips. I entered him again.

Slowly. He was moaning. But his moans were softer now. Softer, with a girly tone. Wow! He was completely surrendered, surrendered to me, to my domination. Was I dominant? How could that be? What a feeling! I could do anything, anything to him. I caught a rhythm. Going all the way in and then out, removing my strapon completely and then shoving it inside him once again. ‘This trick said Jennifer will cause him a little pain, but a sweet pain. It won’t hurt him. On the other hand, it could probably hurt his masculine ego’. Each time I remove the tip and shove it up his asshole, each time I do this is like telling him “hey boy, you are taking it up the Ass, like a little whore you are” so Jen said that perhaps I shouldn’t do it so early, but somehow my body drove me there.

Now I was sweating, my heart beating wild, my boy was under my total control. There on all fours with his asshole opening and closing again. I grabbed him firmly from his waist and kept moving in and out. I was pleasantly rubbing my clit against the soft inside of the strapon. I started spanking him. Fucking and spanking him. Harder and harder. He was burning. His butt cheeks started reddening. Who knows what was going inside his violated Ass. It would take him days to sit again. But who cares? Now I was doing it for me and it was great! I kept moving in and out. Don’t know how long. Opening his Ass, spanking him, marking him forever!

Suddenly it happened. I felt my Orgasm growing inside me. My whole body was shaking, I was coming, coming.

-“Aaaaaa..oooohhhhhh, I am cumin’, cumin'”

“Yes baby, come for me”, my poor boy said.

I grabbed him and fell on his back, bit him, (hope I didn’t cut him seriously) and pushed him on the bed. Removed my strapon from his Ass, his once virgin Ass. I moved to the side untied the straps, and dropped it to the floor. My beautiful Georgia, I will need you again. I kissed him deeply in his mouth. I felt his arms around me. His tongue was exploring my mouth.

Felt his chest on mine. His heartbeat was so strong. We both turned, I was now on the bed and he was above me. He gently opened my feet. He looked me in the eyes, his gaze asking me “Can I?” nodded yes to my lover, to my only Love, I opened my fee, my whole body to him. He entered me softly, gently like never before. He moved once or twice and then he started coming, and coming and coming. All inside me. I didn’t care. This is my man.

I’ll take anything from him.

“I Love you Ritchie.”

-“I Love you Mariah,” he said and covered both of us, under our sheets of white satin.

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