Her first orgasm

This is a true story, only the names have been changed to protect the pleasured.

I was a late bloomer and have never slept with a virgin. Searching for a new FWB, I happened to peak the interest of a woman (Debbie), who at 34 was 10 years my junior. We hit it off at our first meeting and decided to meet again for what would become a year of intense erotic pleasure for myself. And an earth shattering welcome to womanhood for Debbie. Upon saying goodbye at that first meeting Debbie informed me that her husband was her second real lover, and she was seeing a therapist about the fact she couldn't reach orgasm. Never. Not once.

So began a year of regular get togethers. Encounters that started with sex, a little awkwardly, given I was her third partner ever. But second time around things clicked, and she appreciated the talents of my tongue. Not to mention my favourite position, something I call the jockey. From the traditional 'doggy' position I take my partners hands and we lock grip (each gripping the others wrists), thus forcing her face and breasts onto the bed/lounge/car bonnet/restaurant table? We then fuck like crazy as I thrust pulling her hard and deep back onto me.
*Don't try this if the lady has a weak back. I once had a partner re-imflame a slipped disk and spend several days in hospital! Which she couldn't explain to her husband!

Things became increasingly kinky as time passed and she discovered the sexual smorgasbord a Google search delivers. Spankings (that left each of us with bruises for 3 weeks), bondage, light pain, anal play, and sex toys followed. Then came the day she messaged me that she'd discovered 'swingers parties' and wanted to go to one ASAP! That's when things got interesting.

Entirely inexperienced in swinging off we went to a 'girls party', ie gang-bang, with three or so men to every woman. The hosts and guests were lovely but no one was doing anything yet. At the end of our second wine, I whispered in her ear, "how about you slip your dress off and jump on the table for a massage? You'll still have underwear so you won't be naked."
She did as I suggested, two women and eight or ten men watching. Now at this point I must mention how big a step this was for Debbie. Whilst an attractive lady, she did carry the scars of having two children, ie stretch marks, and a little weight. But most of us have physical imperfections, so this never bothered me.
With a little massage oil I started rubbing her shoulders and neck in a firm and relieving manner. While everyone is mingling and watching I bent down and whispered, "is it ok if I undo your bra?". "Okay", she mumbled. So the massage progressed, until Ivan* (not his real name) came over and asked me if she'd like an extra set of hands.
In a hushed voice I asked and she agreed. I moved to the top of the table and worked her neck and shoulders while Ivan sensualy rubbed her back. It seemed that face down, unable to see anyone else in the room, she was loosing her inhibitions. I whispered in her ear that I'd love it if she undid my fly and sucked me. God knows my penis was the hardest known thing on earth at this point.
A little surprised, I immediately felt tug at my pants and her warm moist lips wrapped around me. This continued for several minutes. I lent in and asked if she'd like me to swap places with our new friend, and mentioned that perhaps he would enjoy the same treatment.
I motioned him to swap places as my trousers fell to the floor where they stayed for several hours. Like an ice-pole to the lips on a summers day, his penis was in her mouth!
The massaging continued as I worked down her back and her shapely thighs and butt. Sensing that momentum needed to be kept I asked if she would like her panties removed. Ivan's penis deep in her throat, she mumbled something that sounded like agreeance, and I slipped them down. Rubbing her cheeks, I parted them enough to run a teasing finger around her sphincter, only to find a pool of thick sticky juices flowing from her body. Hopping today would be the day she came, I resorted to another favourite. Sliding my thumb in her pussy I curled my pointer towards my palm, and with slow smooth strokes slid my thumb in and of her vagina, squeezing it and fingers together. Firm pressure on her g-spot and flicking over her clit, I gained pace until I was frantically finger fucking her. She pulled Ivan's dick from her mouth and cried out, "we need to fuck, NOW!"
Aside from myself Debbie fucked three men that day, literally doubling the number of men she had had in her life! It was a good day, but not her day to achieve orgasm.

Our next get-together arrived and we met at our favourite hotel, bags of toys in hand. As usual Debbie got off exercising her dominant side, hog-tying me on the bed, but in such a position that my butt cheeks were wide apart. After a good half hour of the riding crop cracking the inside of my cheeks, I begged for mercy from mistress and she released me.

Now it was Deb's turn. The twin feelings of power and responsibility swept over me. Not power in a dominating aggressive way, but a sense of power, control and responsibility for her body, mind and pleasure. This is a big responsibility every master should take extremely seriously. Being responsible for this woman's sexual pleasure, given its barren history, took the edge off my sexual desire, and despite the scene in front of me, the blood remained in my large head not my half limp penis.

Like an athlete on the starting line I was focused and in the zone. Today was going to be different to our usual games so I started very seriously. "Debbie", I asked, "do you trust me?" Yes she replied. She had no reason not to. We had always had a safe word, on top of that, I'm a sensitive intuitive lover, and while I try and push a partner's boundaries to increase their pleasure, I also know when they can't take any more and need me to stop.
"No Deb, do you really trust your body, mind and pleasure to me, to do with as I please?" Yes she replied. I lent in and kissed her. "Debbie", I said, "I need you to do exactly what I tell you. No questions, no hesitation, you just do it. I'm going to push you tonight. When you tell me to stop I'll slow down, I'll give you a rest, but I won't stop until I decide it's enough. Keeping in mind you have a safe word. Do you agree?"
" Yes", she hesitantly nodded. But the twins of fear and anticipation shone in her eyes. Let's start, I said jumping up on the bed.

"Turn around and undress facing the mirror please". She faced the wall to ceiling mirror and started to rip her clothes off frantically. No, no, slowly and sexily, I instructed. Having always had body issues she hated this, but I thought it important for what was to come. When naked I placed the blindfold on her and started brushing a feather over her as the tingles shook her body. I alternated between the lightest touches of the feather and varyingly intense strokes of the pin wheel. Ohh her scream at the first roll of the wheel over her labia! This was all intended to test her trust and heighten her senses for what was to come. I was also laying a few psychological foundations to build her up with later.

I love a little light bondage, both giving and receiving, breast bondage being one of my favourites. While she found it uncomfortable, Debbie loved the look of her bound breasts, and enjoyed the feeling of pride observing what she had withstood. So I wound my rope over shoulders, around her chest above and below her bust, and started weaving the soft cotton rope in a figure of eight around her breasts. Naturally finishing in increasingly tight loops that puckered each of her double H breasts out stiff, reminiscent of Madonna's early 90's metal bra. The finishing touch; pulling and tying the rope ends. Now I'm not a sadist, so there was nothing extreme here, just firm pink breasts. More pleasure than pain.

"Okay Debbie," I said, "I need proof that I can trust you to put your faith in me. So, I want you to turn and take two steps towards the window". With a little hesitation she obliged.
"Now I want you to pull the curtains open and stand in the window, breasts bound for any one to see".
She paused, understandably frightened to proceed. "Do it now please, otherwise we stop" I instructed. Very sheepishly she peeled the curtains open and took several steps back trying to slither away from the window.
"Step forward again" I ordered. Slowly she obliged. I asked if she'd like the blindfold removed, which she did. Oh the relief that swept her body when she realised the pull down blind behind the curtain was still closed! She smiled at me. "Now you truly trust me? Right?"
Yes she said enthusiastically.

"Do you want to look at these beautifully bound breasts of yours?"
"Yes"
And with that I positioned her in front of the mirror. After taking in my handywork I set them free, the way they were meant to be.

I really wanted to get inside Deb's head, because that's the primary sex organ. So, I had her sit in front of the mirror legs apart, arms behind her head. I asked her to tell me what she saw in the mirror.
"Fat". Was her reply.
"Okay what do you think of? What do you feel when you look at the person in the mirror?"
"No no please don't go there, you don't want to know", she pleaded as an emotional storm brewed deep in her mind.

I wasn't having a bar of it. I had tapped the well of deep dark fear residing within her. I wasn't going to stop until it had been prised open to forever see the light of day! What did her counsellor know? What had they done for her?

"Let's try again", I said, "as I lifted the riding crop and tapped it on her baby belly.
" What's this?", I said with a mildly stinging whack.
" Fat", she replied. NO! How did you get it? I demanded.
"Having three babies", she replied. Correct, I said. What is it? I repeated.
She stared at me.
"It's a battle scar Deb, it may not be the prettiest thing in the world, but you damn well earned it. Be proud of it! If a bloke had a flabby tummy from child birth we'd brag about it like it was an old sports injury. Did any of the 20' something's at the swingers party diss you because of your belly?"

No they didn't, but she remained silent.

Whack, I slapped the crop across a breast. Tell me what you see? I requested.

" Saggy boobs " came the reply. I repeated the same speel as I had about her tummy. All to the same response.

A little unsure if I was on the right path, I pushed on with a swift stroke to the top of her pubic mound. "Get your legs wide apart and pull your lips open", I instructed, she obliged.

Tell me what you see? I requested. She stared at me, the emotion building deep within her. As there was no response I posited that, perhaps she didn't like her vagina? Again no response.
"Well I like your pussy", I said. I wouldn't be here licking you if I didn't. All the guys at the gang bang liked it. Do you remember when you were in doggy being fucked by Trevor* (not his real name) while you were sucking that other guy off? Do you remember what Trevor said to me? "

No? She looked intrigued.

Remember Trevor was the good looking guy about 25? He turned to me, as he's frantically banging you and said, "You are one luck man to have a woman like this!"

"Yes really. Who was the first woman at the gang bang to get naked? And do so in front of a dozen strangers?"

Me? She mumbled.

"Right. Who was the woman who started sucking dick in the open room while everyone else stood around awkwardly?"

"Me".

"Who got naked and finger fucked while all the shy people stood around fully clothed?"

"Me."

"Who fucked as many men in an hour as she had in her entire life?"

"Me!"

She could see what I was getting at.

"Okay up on the bed and blindfold on please". She eagerly jumped up, a new sense of vigour about her.

The following hour consisted of me delicately licking her pussy, applying, removing, reapplying and then tightening nipple clamps. Pin wheels all over her body. Frequently she pleaded with, even ordered me to stop, but she never used her safeword. I backed off, gave her the time to calm down and then got back to businesses. The pin wheel over her clit was torture but she loved it, and increasingly wanted it harder and harder.

All of this was building towards her climactic suprise.

I slowed down for a few minutes, removed the blindfold and we kissed. I assured her she was beautiful and a lovely person. The only person unaware of that fact was Deb unfortunately. "Okay. Now it's time for your suprise".

After everything this evening she looked a little worried. So, I requested she close her eyes. "I've bought you a present", I said, "it's yours to take home and do what ever you want with". I slid the magic wand I bought from under the bed and placed the head on her clit. She moaned a little. Unsure what it was. "How does that feel?" I enquired.

"It's okay", came the response.

"Oh fuck," she screamed opening her eyes as I turned it on. She quickly grabbed a pillow to muffle her cries. Wanting to capitalise on her euphoria I slid to fingers in her pussy and stroked her g-spot in the come-hither motion.

It was too much and she pushed the toy away. "Deb, I'll let you rest, but we don't stop until I decide its enough".

Yeah-yeah she panted.

I let her regain composure for a minute and intensified the action of fingers and toy. Every time she went to push the toy aside I backed off or distracted her. "DEBBIE, who was the girl who got naked in front of a dozen strangers at a gang bang?"

"Me", came back a sheepish whisper.

And on it went. Every time she wanted me to stop I said no, not yet. I backed off a little or distracted her by asking, who was the woman fucked by as many men in an hour as she'd had in her life? Who sucked a stranger's cock in front of a dozen strangers Deb?

Every time the answer was the same. Me. Me. But it had an increasing decisiveness about it. No more shy whispers of me. It was begging to be a thundering chorus of Me Me! ME!! Faster and more intensely I went, I turned the wand to high. She stopped pushing it away. And I barraged her with questions.
Who sucked a stranger's dick and loved it? Me!
Who got naked in front of a dozen strangers? Me!
Who got finger fucked in front of those strangers? Me!
Who loves fucking men? Me!
Who did young guys want to fuck? Me!
Who has a beautiful pussy? Me!
Who's fucking hot and loves her body? Me!

And like the first crack of thunder from a summer storm, the flood gates opened wide. As she screamed into the pillow I pulled the toy away and tried to twist my fingers so as to not get my knuckles ground by the force of her vagina in full spasm.

She looked up at me, a sly grin on her face. "What do you call it when the muscles in vagina, and rest of your body contract in uncontrollable spasms Deb?"

"An orgasm?" she giggled.

The end.