First Bondage Encounter

The first experience for me was February 2001. So yes, I am new into the alternative life style. I am glad that I made the step to find out myself of the BDSM world.

In August of 2000, I went to the dungeon at Ms. Desiree's in Bangor Dungeon in Bangor, Maine. Surprise, Maine has well guarded secrets too. She is also my youngest sister, so I was aware of the alternative life style but had not seen first hand. I watched her with a client, took pictures for her as she took him thru his fantasy of being tortured while a woman watched. It was important that he be humiliated in his fantasy, so I got my first visual experience.

Six months had passed and my thoughts still wandered back to what I had watched. I was curious, and drawn to what I had seen more than I wanted to admit.

I was visiting with my sister, when a client of hers arrived unexpectedly. Janessa was excited and wanted to show Desiree his new outfit. I met Janessa, a cross dresser I had seen on her web site. A very interesting man that was fascinated with woman's clothing. He got very aroused with the feel of woman's lingerie in the beginning and then the total look.

I watched as he made himself into the woman, the sluttish bitch image that he was the most aroused with. I was amused to see the amount of make-up he applied. I couldn't help myself; I began helping him with his make-up. I pointed out tips that made applying easier as well removing quicker. I showed him different ways to apply eye shadow to give a more Asian look, exotic look that was more appealing then the cheap look that he was used to. Janessa had chosen a leather skirt with a leather vest to match that looked very attractive on his lithe figure.

We began discussing the role exchange. How he felt with participating in the role-play with a man or a woman. He said, "thus far I have not dominated a woman dressed as a woman."

I asked," why not?"

He smiled as he replied," most women are more comfortable submitting to a man."

Now, my curious nature got stimulated, I asked more questions about the actual exchange." What did he do as a Mistress that was different then as a Master?"

He /she smiled, replying that I would only know if I experienced both.

I glanced over at my sister," how would you feel if I was naked being submissive to him."

He spoke up, to her; I am going to be dressed as I am? I am Mistress Janessa to you.

She shrugged," if it bothers me then I'll leave."

I asked," are you sure?"

She smiled as she replied," Janessa, enjoy yourself because her true nature is dominant and this will probably be your only chance."

I went to walk into the dungeon; Janessa speaks sharply," only the chosen ones may wear clothing. Strip now!"

I looked one more time at Desiree. She picked he camera up, snapped the first picture of me in front of the door. I unbuttoned my shirt, slowly looking directly at Janessa as I did.

Janessa turned to Desiree states, "she needs to learn her place; apparently she feels she is an equal." I continued to undress, never taking my eyes from her.

Janessa says," Come to me"; she fastened leather wrist restraints to my arms. Then taking my arms hooking me to the 4x4 posts on each side of me. She then did the same with my legs, taking her hands squeezing my inner thighs hard before rising. She then picked up a whip, snapping it in the air, smiling ear to ear." Should I use this heavy whip and bruise you for your arrogance or should I flog you with the soft deerskin flogger and make you beg me to let you cum?"

I laughed and said," I never beg for anything."

He snapped my bottom with the whip;" speak only when I address you. I will expect you to count as I discipline your impertinence." He took the flogger down, and began with that on my bottom.

" Yes, Mistress, may I have another. 1 Mistress, thank you, yes Mistress, may I have another. 2 Mistress, thank you, yes Mistress, may I have another."

The routine of the expected response was fine but the distraction of the flogger as she whipped my breast as well, made me forget the correct number of the count. That meant we began again, I was feeling many feelings that I hadn't expected. I was feeling aroused by the flogger or the scene itself. I wasn't sure only knew that my body was on fire and not with pain.

Janessa ordered me to kiss her lips now!

I looked at her, and hesitated briefly the image of a woman before me, but I knew was a man. I went to kiss her.

She grabbed hold of my nipple wrenching it hard telling me that I was to obey prompt not when I felt like getting around to.

"Yes, Mistress," I then kissed her, the taste of lipstick on my lips, the smell of her perfume hitting my senses as I did. I felt so aroused by this time to turn back, I need to know more. I looked at Janessa, smirking as I did," is that all your wuzzy little hand can do." I laughed as she got flushed in the face. I watched the facial exchange between her and Desiree.

Desiree looked at me," be careful of how far your push your need to feel."

I grinned and reminded her that we had known worse as a child.

Janessa took the heavy whip and began again, telling me to count as before. I did but she wasn't satisfied that I was feeling the whip as she needed. She picked a paddle from the selection on the wall. Holding the paddle in front of my face, told me," kiss the paddle."

I said," Kiss it yourself." That made her angry that I was not remaining submissive. She took great pleasure in warming my bottom.

"Yes Mistress," I counted, "one", "yes May I have another?"

Then she decided that my nipples weren't aroused enough to suit her so she twisted them till they were taut then added the nipples clamps too. Oh the sensation was incredible as she paddled me and I thrusted my body with the blows that making the clamps move with my body movements. I was very turned on, Janessa flicked her fingers on my breasts, teasing them with stimulation that was pain as well as stimulating me. I was flogged a few minutes longer after she laid the paddle aside, deciding to make me feel more than she was getting with the paddle. She would strike my cheeks one time then come between my legs striking the underneath side of my pussy lips.

Oh that got my attention, quickly, making me whimper as I thanked Mistress may I have another. Desiree took pictures as she was punishing me or pleasing me but I had totally forgotten about her presence.

Janessa released my arms from the restraints; the tingling sensation of my arms was a weird feeling from arms being taut as they were. Janessa then released my nipples from the clamps. That was intensely painful as the blood rushed back to my nipples, I leaned down to undo my legs as my breasts touched my thighs I felt pain and pleasure as they touched my leg. I moaned in a delightful sigh.

Desiree walked away from the room. Janessa held my arm for a minute. Reaching down to my pussy, inserting his finger then withdrawing it, smiled and then inserted it into my mouth." I know, you had an orgasm; I saw it in your eyes. You are more submissive than you know. You were made for pain and pleasure games, go with your feelings. Explore them honestly; you will be amazed at how much you haven't felt yet."

I have thought about that day and yes I learned that I was submissive as well as dominant. The exchange, trust was something I was unfamiliar with. The need to push Janessa to hurt me surprised me. The image of him as a woman reminded me of the curiosity I felt about being with a woman. Was I turned on by her dress, a little, but not as much as I was by the feel of the flogger and the pain, the stimulation to my breasts? I have seen her in many different dress situations and none have aroused me as that first time did. I didn't submit again to her, only took pictures as she took men dressed as a woman.

Janessa has done a couple more scenes with different women; she actually found that dominating a woman was more stimulating then with the men. So taking the initiative to seek more learned lessons for all.

Have I submitted again? Yes with a man as a woman. I will share the second occasion as my next contribution. Try it; attempt the exchange, as foreplay you will discover lots about yourself that you was unaware of. Remember the safe word, trust each other, and communicate.