I have been seeing Headmistress Sade for almost 5 years. She has taken me to many new heights in my own personal journey. Notable was the day, May 25th, 2007, that she gave me my first (few dozen) prostate orgasms. Since then I have had many hundreds. Over the years I have also come to trust her implicitly – her skill, her sensitivity, her intelligence, her eroticism, her sadism, her control, her honesty, her sense of humor and her integrity.
Some months ago I met Priestess Anness, a young transsexual woman who is beautiful – tall, lithe, slender and oh so flexible. She is also sensuous, warm and very, very kinky. We since have played together several times. The first time she was my Domme. Over time we have had a variety of experiences from BDSM to sensuous to therapeutic (massage) experiences. During our talks, I learned that she liked to switch. Since I have wanted to try topping for some time now, I asked if she would let me top her. She agreed. In addition to BDSM, Anness is also very interested in anal and prostate stimulation.
When we met I brought my whole kit of toys – including my Lilo Elyse vibrator. It was my first time ever as the Dominant, and while it was fun for me I realized I went too far too fast for her. I basically topped her the way I like to be topped – a mistake. I am a fairly heavy player – into pretty intense sensation. I like to build up to it pretty quickly. When we moved onto anal play I used my, extremely powerful Lilo vibe – it was just too much for her. In our after session debriefing I recognized that I had topped her the way a man would like, not a woman. I realized I needed some instruction in how to top a woman.
Naturally, I could think of no better person than M. Sade. So I asked Anness if she would be willing to have me take her for a session with Sade. Once I had described Sade to her, and her incredible anal and strapon skills, she agreed.
Next came the more interesting part, asking M. Sade if she would play with another person, a transgendered woman, while I was present. I explained that I would just watch, but that I wanted training in how to top a woman. Once she agreed I set up the meeting.
My Lesson (A Surprising Cuckolding)
I arrived about 5 minutes late, due to traffic, and found that the Anness had already arrived. M. Sade greeted me and I saw that she and the Anness had been chatting for bit before I arrived. I had to use the washroom to cleanup, and M. Sade got ready as I took a quick shower (it was a hot muggy day outside).
When I returned to the room Sade had changed into a very sexy fetish outfit and it was time to start the festivities. I stood to the side of the room, outside of their line of sight so as not to interrupt the dynamics between them. Anness pulled her top over her head and M. Sade stopped her. “Well, if you are going to strip, I want the whole thing – do a striptease for me.” (Which brought me back to my earliest days at Rapture, when a number of the Dommes liked to begin their session by having their subs do a, usually clumsy and humiliating, striptease.)
I knew however, we were in for a treat, because, Anness has danced and stripped on stage. M. Sade went to her I-Pod and put on a mix of Morphine and Portishead – slow, very sensuous music. Anness began to seductively move to the music. Using her incredibly long limbs to stretch out each move. As she bent over, shaking her ass, M. Sade stepped in behind her, put her hands on her butt, and leaned over and whispered in her ear. I could not hear what was being said, but it obviously inflamed Anness. Her nostrils almost flared, and I could see her sigh in response. Her body slackened as she visibly responded to the words. I felt more than a twinge of jealousy. What had she said?
Stepping back Anness continued her dancing. She turned around, back towards us, and removed her top. She dragged the top across her back, over one shoulder then the next. Turning around she slid the material across her breasts and revealed her small but very perky breasts. Her nipples were rock hard. She tossed the top away.
Turning back around again she bent over, looked back at us and rocked her hips from side to side. She did it slowly, in sync with the music, incredibly sensuously. It was an open invitation to ravage her. M. Sade stepped in behind her again. Then I noticed the black leather gloves she was wearing. They were vampire gloves, the palms covered in tiny pinpricks. M. Sade softly, gently, drew the gloves down her sides and flanks. The pinpricks left no marks, except in Anness’s mind. It was obvious that the shocking sensation excited her. Bent over as she was, I could see Anness melt into M. Sade’s caresses.
M. Sade removed one glove and handed it to me. Now she alternated her caresses, her left hand sharp pinpricks, her right hand soft caressing skin. Anness almost whimpered in surrender to the sensation. M. Sade then again leaned over her back and kissed the back of her neck and the lean muscles in her upper back between the shoulder blades. Oh so soft, moist, tender lips on oh so soft, silken, sensitive, longing, skin. M. Sade then moved around to her side and kissed her ear, slipping her soft wet tongue inside. (Damn!) She then licked around the sensitive skin around the ear and down the neck to just where the jaw begins.
Stepping back, Anness continued her dance. Turning around, her breasts and hard nipples thrust forward at us she leaned back and began to remove her jeans. Thrusting her pelvis forward she began to unbutton her jeans, then slowly slid the zipper down ward. Again rocking her hips from side to side, she slowly slid her jeans over her thighs, down to her knees. Stepping out of her shoes she slipped the legs off one after the other. Tossing her jeans aside she was left standing in her grey silken panties.
Turning around she leaned over the chair that was there. Her butt thrust out. M. Sade again stepped in behind her. She thrust her leather-covered pelvis into Anness’s butt and ground it into her. Using her hands, one soft, one spiky, she caressed the outside of her thighs, then moved them slowly up the inner thighs. [It was so fucking hot. I longed to be Anness, feeling those deeply contrasting caresses.]
Anness was obviously lost in the sensuality of it all. M. Sade, took off her other glove and handed it ot me. She put her hands around Anness’s neck. She just held them there for a second. Waiting. Anness gave a tiny, almost invisible nod, and M. Sade began to squeeze. Watching her face closely she choked her. You could see Anness surrendering into M. Sade’s grip. After about a minute she released her grip, kissed the back of Anness’s neck and stepped back.
Anness stood and slowly removed her panties. Turning her back she slid them down her legs and completely off. Draping them in front of her she turned to face us. Dropping the panties she revealed her cock(clit?). It was as erect as her nipples. Her eyes were almost glazed in lust.
M. Sade took her hand and led her over to the bondage bed. She had her lay down on her back, then kissed her lips and caressed her. I put the gloves on top of the stand, then picked up Anness’s clothes and hung them on the post of the throne chair in the corner.
M. Sade took her time gently caressing Anness – her arms, her legs, her sides. She kissed underneath her neck then worked her tongue down her chest. Sucking on her nipples she stayed for a minute, softly biting them. Then sticking out her tongue she continued to work down her chest and belly to her navel. She stopped there a minute. Then continued down her pelvis to her inner thighs and down her legs. Anness just surrendered into the sensation. No torture, just pure unadulterated pleasure.
Taking a small zippered pouch M. Sade removed a bullet vibrator. Turning it on she touched it first to one nipple, then the other. She then stroked all along Anness’s body.
Stepping over to the table M. Sade donned a pair of black nitrile gloves. She double gloved her right hand. “Next time, I get powdered gloves, so it is easier to double glove,” she told me.
Reaching into her pouch she took out a bottle of Astroglide and dripped some onto her fingers. Anness pulled her legs back over her head awaiting the touch of those lubed fingers. I took hold of her ankles to giver her some support. M. Sade then sat on the table and reached between Anness’s thighs. Taking the bottle of Astroglide she dripped some down into her pussy. She then began to rub her fingers around the entrance. Softly caressing the entrance. Making her long for penetration (trust me I know that longing). Then she softly slipped a well-lubed finger inside. Moving her fingers slowly she spread the lube around, gently dilating the sensitive orifice at the same time. Slipping in another finger she continued. Removing her hand she discarded the outer glove and dripped more lube onto her fingers.
Time to get serious. She slipped two or three fingers inside (I could not see for sure) and began to fuck Anness with her fingers. As they slipped in for real I heard Anness gasp. M. Sade slowly fucked her. Building the speed and intensity slowly until she was pounding away. It was too much sensation for Anness, so they discussed something for a few moments and then M. Sade subtly changed her motion. You could see Anness responding to the sensation, but she could not quite let go.
Almost in frustration M. Sade told Anness to work herself onto M. Sade’s fingers. The sight was amazing, Anness’s long, lean body fucking herself on the black fingers of M. Sade’s glove. You could see the blazing lust in Anness’s eyes as she tried to work to release, but she could not quite get there. After several minutes she slowed and relaxed.
M. Sade stepped back, and removed her gloves. She grabbed her strapon harness and strapped it around her hips. Taking a small to medium size black dildo she slid it into the ring in the harness then snapped it in place. She then pulled a condom over the dildo and dripped lube onto it then rubbed it all over the dildo.
“How do you want it?” M. Sade asked. “I want to see you, so, on my back” Anness answered. Sliding onto the bed beside her M. Sade slipped between Anness’s thighs, which she then pulled over her head. As M. Sade moved her body over Anness’s, she positioned the dildo at the opening of her pussy. Slowly she thrust her pelvis forward and the tip began to enter Anness. Anness’s mouth opened slowly, then she let out a gasp.
M. Sade then began to slowly, sensuously fuck her. It was one of the most erotic, sensual, loving things I have ever seen. Their bodies touched each other all over as they moved. I was so incredibly jealous. At once, I wanted to be M. Sade, giving such pleasure to Anness, and at the same time I wanted to be Anness, being made love to by M. Sade. I was cuckolded. I was doubly cuckolded. It was thrilling to watch, but I felt I was such an outsider.
I watched M. Sade, who is the best strapon fuck I have ever known, use all her gentle skill on Anness. Slowly her orgasm built, until finally, with loud high-pitched squeals, she came.
M. Sade lay over Anness for a minute as they came down, then slowly slipped out. They lay huggin and caressing for a few more minutes. I didn’t hear exactly what was said, but M. Sade laughed and Anness giggled. Once she stood, M. Sade looked over to me, “Any questions?”. “No.” I answered.
I knew that the two of them would get along, but I did no expect the sheer lust and heat that exuded from that room.
May we all have such erotic, intimate moments.