Written by Bessi April 10, 2019
Another training, in yet another strange city. Oh how I hate these things. It is beyond me why they can’t do like everyone else and have this online. I guess the bright side is getting to meet new people and network. Maybe learn the history of a place I probably would never have visited. I do wish my beloved could have come with me to experience it too. So, after a long day of grueling training sessions, I head back to my room. I begin to wonder about the nightlife some of the others were chatting about. They seemed excited about the prospect of unwinding in the downtown clubs. I order some room service and call back home to check on my sweetie. Everything seems to be in order and I tell her that I miss her and that I may check out the local scene for a bit. I google the hotspots and find a nearby club that seems to cater to alternative lifestyles. It is a place that I did not hear the other training attendees mention, they don’t know what they are missing I think to myself. I call an Uber and off I go to check it out. It is early evening and the club is beginning to get crowded. I find a table off to the side where I can observe everyone and order a glass of wine. I notice a mix of people in the crowd and everyone seems to be thoroughly enjoying themselves. After about an hour and about the time I am ready to call it a night I notice a tall woman in a short red dress that is very revealing. I watch as she nervously moves around the room, dances with people that must know her. She seems uneasy as she moves around but loosens up after a few drinks. I later see her sitting at the bar and decide I need to get a closer inspection. I sit beside her and smile. She smiles back but does not say anything. I decide to break the ice. I have never been hesitant to take control of these types of situations. “Hello, I am Camille.” She replies back, “pleasure to meet you Camille, I am Bessi.” “So tell me Bessi, how long have you been dressing up? I must say you have done a wonderful job. I do love the look you have chosen.” The poor girl gets a panicked look so I put my hand on hers and say, “Relax sweetie, its okay. Your secret is safe with me.” I can see the tension fade a bit so I tell her, “It would please me greatly if you would go back to my table so we could chat.” I stand up and begin to head back to the table I was at which is thankfully still vacant. Bessi follows and we sit down. She straightens her dress and crosses her legs because as I said, it is a very short dress. “So where were we, oh yes, how long have you been cross dressing?” Bessi replies that she has dressed up for many years but has never been out in public before tonight. She ventured out at the encouragement of her friends and was very nervous. I ordered us both some wine and told her that I was in town for training and I had decided to check out the local scene. She welcomed me to her fine city and asked what I thought of the place. I told her that I liked what I see so far and she blushed. Bessi went on to tell me that the city was fairly open to alternative lifestyles, had several clubs that most would call tranny bars and even had a dungeon or two for those into those kinds of things. This piqued my curiosity. I asked her, “so are you into the whole dungeon, bondage and submission lifestyle Bessi?” She replied, “I have been fortunate to meet a few good Dommes and do some play sessions with them. I must say it was very exciting.” I told her, “very nice, you should know that I am one of those Domme types. My specialty is actually boys that like to be girls. My girls call me Ms Darklady. “Well then it is truly an honor to have met You Ms Darklady,” Bessi replied. She went on to say that her friends had pretty well scattered and that she thought she would take the opportunity to slide out. I asked if she would be a dear and give me a lift back to the hotel. She agreed and we left. On the way back to the hotel I asked Bessi, “Bessi my dear, I would love to chat more about your experiences as a submissive. Would you be interested in coming up to my room so I can see how well trained you are by these local Dommes? I didn’t pack for the occasion but maybe I can find some items that could be useful.” Bessi replied, “I actually would love that Ms Darklady. I have a confession though, I have a toy bag packed that might enhance the evening for You should You wish for me to bring it.” “Well aren’t you the little tart. Grab the bag and let’s go. Bessi parked in the hotel garage and walked around to open my door. She grabbed the bag and followed me up to the room. Once inside I tossed my purse onto the table and sat down while Bessi put the bag beside the bed and then came over and knelt at my feet with her hands across her lap, open palm. “I can see that you have been trained a bit. Did any of these Dommes instruct you on what to do about aching feet?” Bessi replied, “Yes Ms Darklady, they did.” And with that she removed my shoes and began to rub my feet. She then began to kiss my feet and eventually had my toes in her mouth. I told her, “don’t stop, I am going to call my wife and let her know I am safe.” “Yes Ms Darklady, as You wish,” was the reply. “Hey sweetie, yeah I am back in the room. Yes the nightlife is rather robust. You should see this sissy bitch I met. Yes, she was dressed to the nines. As a matter of fact, she is kneeling before me sucking on my toes. Ok sweetie, love you too, yes I will snap a few photos for you,” I told my wife. “Ok Bessi, let’s see what you have in your toy bag.” I opened the bag and found a rather large dildo, strap on belt, nipple clamps, lube, latex gloves, and a small flogger. “Well let’s test some of these out shall we,” I told Bessi. I instructed her to kneel over the end of the bed which she immediately did. I put the nipples clamps back in the bag, “we won’t need these since they won’t do any good on your fake titties so let’s start with this,” I told her. I then grabbed the flogger and lifted her dress. “Oh, nice thong my slutty little girl”. Over the next fifteen minutes I worked each cheek, eventually getting a nice color on both that beautifully matched her red dress. I then slipped on the strapon and put a glove on and squirted ample lube across the fingers. I pulled the thong to the side and saw a pretty jeweled butt plug. “My my, aren’t you just the prepared little sissy,” I told her. “Yes Ms Darklady”. I then worked my fingers in and out her tight hole and lubed the end of my plastic dick and put the head against her rosebud. “Now be a good sissy and back yourself onto my cock and show me you want me to deflower you,” I commanded her. She did not speak but slowly pushed herself back and had the entire length in her in no time. “You are such a hungry slut tonight aren’t you Bessi?” She did not respond quickly enough so I gave her a stinging slap on her ass. She moaned, “yes Ms Darklady, I am your greedy little slut. Please make me Yours.” Thirty minutes later we were both out of breath. I pulled her up and whispered in her ear, “you did wonderful, but you have made me so wet and I expect to be properly cleaned up. Lay on the bed my sissy slut” she spun around and lay on the bed while I dropped the harness to the floor. I shimmied out of my panties and proceeded to sit on her face. “Lick it bitch.” I controlled her air, bringing her to the point of passing out before raising up slightly every now and then to allow her to gasp for air. Not once did she attempt to push me off and actually pulled me tighter at times. I rode the waves and eventually fell to the side. I smiled at her and told her that she had been trained very well and she thanked me for the compliment. “Bessi, I had a wonderful time but I have more training in the morning. Before you go, did I see a muscular guy give you his number at the club?” “Yes Ms Darklady, he did give me his number”, she replied. “Good, when you get back to your car I want you to call him, meet up with him and be a woman for him. I expect photos no later than sunrise in the morning. Do you understand my sissy slut?” Yes of course Ms Darklady, as You wish,” she said. “Here are my details on a site called FDS or femdommesociety.com, go there and make a profile and find me,” I told her as she gathered her stuff and went to the door. She turned to look at me and smiled, “thank You Ms Darklady, it was an honor to be your sissy slut”. And by the way, you should see the photos I received at 6am
Well done bessi but this was written in April , the girls must be waiting for the follow up i helenah cissy certainly am .
awesome story...bringing out the best in Her submissives as only Mistress DLC can do. alyssa
Wonderful story Miss I do envy Bessi
What a sexy story... and one that's definitely made me a little moist to say the least!