First Strap On experience - Part 1

I had finally given in to my darkest desires and gone to a dominatrix. We had met online and chatted quite a bit before finally meeting in the flesh. At first, I had been a bit embarrassed and more than a bit uncomfortable.

She called herself Alexandra and she was not at all what I expected.  Quite quickly, I found myself relaxing and opening up to her. She smiled and appeared down to earth and sensible.

After the initial pleasantries had been dispensed with, I told her what I had in mind. She told me the price and after I had paid it and assured her that I wasn't a cop; we proceeded with what I had asked her to do to me.

Chapter One – Bound and Whipped

She led me into the soundproofed basement of her modest middle-class house on a double lot in the middle of suburbia.

There, in the darkness of her improvised dungeon, she had me strip down before she attached fur lined leather cuffs to my wrists and ankles.

Heavy duty cables were also attached to the cuffs. She walked over to the wall, she flipped a switch. There was an electric whine as several winches slowly tightened up the slack in the cables.

In the end, I was bound spread-eagled.  My arms and legs held firmly apart. I wasn't uncomfortable but I wasn't going anywhere, either.

"I'm not going to gag you, this time." She said from slightly behind me, in a conversational voice, "I will have the answers I seek before I gag you."

She was still dressed casually and I did not feel afraid, even though I was bound nude in a strange woman's basement.

"Just to be clear; you want me to masturbate you and then whip you while I question you about your darkest desires?" She asked.

"Yes!" I said as clearly as I could.

"All right" She said warningly, "I will point out to you again the two provisos I stated over the net when we met. One, I cannot stand whining. Whine and we are done!"

I nodded clearly, hoping she would see me.

"Two, I am aroused by this shit! I enjoy tormenting men but I must know that they want me to torment them. Your safe words, are as we agreed; 'red' and 'yellow'. 'Yellow' means slow down but 'red' means stop." Her voice remained calm but I could hear an undercurrent of tension beginning to build.

I nodded again and repeated my safe words so she'd know I had heard her.

"Then let's begin." She said from behind me.

I heard her stilettos click as she walked out to stand directly in front of me.

The light above me also showed her. She stripped naked behind me and then, she put her high heels back on.

She stepped back into the inky darkness momentarily only to emerge with a riding crop.

I felt my breath coming in short gasps at the sight of her.

She stepped close to me, her hungry eyes eating up my bound nude muscularity.

Reaching out, she grasped my sensitive and vulnerable manhood with calm menace.

I gasped at the intensity of her act. She smiled ruthlessly as she rhythmically squeezed and released my growing erection.

I held as still as I could and drank in the profoundly erotic sensations. Very quickly, I was sporting an iron hard erection. A bit of precum leaked from the head of my hard, red erection as it stood proudly out before her.

She smiled down at what her efforts had produced and said calmly, "So, you can be aroused...Let us see if you can maintain it when I discipline you?"

I gasped again as she walked behind me, her hand trailing over my bound nudity as she set herself ready to whip me.

I heard her speak to me from behind as though I was in a dream.

"I will ask you only once. If I have to repeat myself or if there is any hesitation in your reply; I will punish you." She stated calmly, "Do you understand?"

When I was a bit slow in answering, her whip whispered through the dark basement air before landing with a sharp painful crack on my nude and bound body.

I arched and groaned in response.

"Do you understand?" She reiterated more sharply.

"Yes!" I gasped.

I heard the whip in the air again and I gasped in pain when it landed.

"You will answer with ma'am, as in 'Yes Ma'am!" She corrected me before stating, "Now say it again and do it correctly this time!"

"Yes Ma'am!" I gasped as she lashed me again and again.

I groaned and flinched.

She laughed at my response to her torment.

"I remind you that I get off on all this! Not only are you going to pay me a lot of money; I'm going to enjoy your suffering!" She snarled from behind me.

She lashed me again and when I refused to whine or whimper I felt her press her naked body against my burning back.

"Your defiance pleases me! See that you keep it up! But I also want you to know that breaking your spirit shall be sweet!" She whispered cruelly.

I knew that this was all part of the game we had agreed to online before we had ever met. I also knew that I could have used my safe words to cool down the action or stop it completely.

The truth of the matter was that I didn't want to. Even though my erection was now gone, I knew she would bring it back momentarily.

I was correct and as she pressed herself against me, her knowing hand snaked around to possess my flagging member. She began to rhythmically squeeze and release my cock.

I groaned in passion and growing pleasure. This woman had been paying attention when I had told her what I was aroused by.

I could feel the heat of her naked flesh on my nude and bound body. Her breath was sweet and warm against my ear as she humped the back of my thigh while slowly masturbating me.

Chapter Two – The Questioning Begins

Suddenly and without warning, she stepped back. There was a slight pause before she started her questioning.

"Are you sexually aroused by being bound?" She asked.

Obviously that was the case and I answered, "Yes, Ma'am!"

"Are you sexually aroused by being sexually touched and whipped while bound?" She questioned.

Again I answered in the affirmative.

"Uh...no, I'm not...ma'am." I answered hesitantly.

I heard her whip whisper through the air before it I felt its fiery kiss on my muscular backside.

"The only answer I will accept to any of my questions is 'Yes, Ma'am!" She snarled from behind me.

"But I have never been anally violated and I'm very reluctant to try it." I answered rather defiantly.

This then, was the crux of the matter; would she be able to dominate me in an acceptable matter and force her will upon me or not?

"Well then, it will be a new and fulfilling experience for you, won't it?" She purred.

"I...uh...I don't..." I started to say.

She lashed my backside again before reiterating, "The only answer I should hear out of your mouth is Yes, Ma'am!"

I hesitated and she struck my arse with her whip again.

"Are you sexually aroused by being anally violated?" She asked more impatiently this time.

"No! I don't want to be fucked up the arse!" I said defiantly.

I had chosen to be defiant, I thought, "Let's see how you handle this?"

There was a pause before she said calmly, "I see. Well, there is only one answer for that!"

I heard the whip whisper through the air and had just enough time to tighten up before it landed on my backside.

Again and again she lashed my bound and nude body. She kept her lashes to my arse but they stung all the more for being restricted to one area.

I flinched and struggled to keep from gasping.

"Will you answer correctly?" She snapped at me.

"No!" I gasped, a bit breathlessly, "You can't make me, either!"

She laughed ruthlessly before stepping close and grabbing my now totally soft cock.

With a few expert squeezes, she had me iron hard. I could feel her hand on my privates. I could feel her hot body pressed against me from the side. Her breath in my ear was like an aphrodisiac.

I struggled not to let her see how aroused I was by her actions.

"Maybe I'll just gag you and rape you without your consent? How would you like that?" She asked mildly, her body pressed tightly to my nude and bound muscularity.

Just the thought of her having her way with me was enough to make my now iron hard erection just that much harder.

I felt both aroused and appalled.

When I hesitated, she continued to squeeze and release my now iron hard prick but she said, "I think your lips are saying no-no but they lie. It's your iron hard cock that I'm listening to."

I gasped at the intensity of her torment and found I had to struggle not to give in.

She laughed and with one final squeeze of my dick said, "Answer me in the affirmative or I'll give you twenty five strokes on your backside without pause."

I lifted my head proudly and clenched my jaw so she would see that I would not give in.

"Have it your way." She said warningly, "Once I start, you'll receive all twenty five regardless of when you give in."

I heard the whip move through the dark basement air. It gave me another fiery kiss on my taut backside. This stroke was much harder than the previous ones.

I gasped in pain but there was no time to recover as she lashed again in quick succession. The following strokes were also very hard.

Around the fourth or fifth stroke I began to gasp and around stroke number ten, I began to groan and flinch in pain.

"Do you want me to fuck your virgin arse?" She asked without bothering to pause in her lashing.

I shook my head in defiance and she laughed before saying, "Good! I had hoped you wouldn't fold, over a little pain."

Around stroke twenty, I began to cry out as the lash landed.

After the last stroke; I heard her question me again, "Shall I gag you and use your arse for my own sexual gratification?"

I shook with effort and pain but I refused to give in. Instead, I shook my head without bothering to answer.

I heard her stilettos click as she stepped close to me. Her hand softly caressed my bruised and tender backside.

She walked in front of me so I might see her clearly.

Softly and carefully touching my now soft manhood, she looked deeply into my eyes before asking, "Don't you find me attractive enough to fuck?"

My cock began to rise at just the thought of penetrating her. She knew what effect she was having on me too. She smiled.

"Your hardening cock tells me you want to service me." She said coyly.

I looked away in embarrassment as I knew she wanted to use me in a way I had never been used.

She changed from squeezing and releasing, to stroking my growing manhood. I could feel myself becoming even more aroused.

"I tell you what; I'm going to gag you and I'm going to fuck you and there is only one thing you can do to stop me." She said softly.

I knew what she meant. If I said nothing, I was implying consent. I watched in horrid fascination as she turned and stepped back into the darkness of the basement.

She returned a moment later. Around her waist a long thick plastic dildo bobbed obscenely. Obviously it was well lubricated. Some of the lubricant actually fell from the monster as it bobbed in counterpoint to her steps.

In her hand, she held a large ball gag.

She smiled knowingly and I could feel my passion building along with my fear...

(cont'd)