[NOTE - Anyone who is just beginning to read my blog might want to read the following early entries in my blog about my sissy journey before reading this latest entry: - - - - - - - - - - - - - - - - - - - - - - - - – - - - - - - - - - - – - These are the previous posts that tell the story about my sissy journey.]
I am in a bit of trouble. Quarterback has kept us quite busy over the past two days, but he told me he expects me to keep up with my reporting on my blog. Thus, it is currently Day 4 and I need to report about Day 3, a pretty intense day for me, and probably my cheerleader as well.
I have been waking up earlier than everyone else since we arrived in Mexico. My clock hasn't readjusted quite yet. Thus, I have spent the first few mornings in my bedroom waiting for quarterback and cheerleader to wake up. On Day 3, Mercedes came to my room to help me get dressed for the day just after I heard quarterback and cheerleader stirring in their room next door to mine. She told me to shower and shave smoothly all over. When I returned to my room, she had my "outfit" for the day lying on my bed. I was going to be a kitten. She was smiling at me as I entered the room and teased me in the sweet way she had developed with me, "Here kitty. Meow!" And then she giggled. I felt embarrassed, but not enough to make me feel bad, as I had grown comfortable with her attending to me. My cheerleader had, apparently, brought the tight shorts with the crotch sewn open in the rear to accommodate my butt plug and kitten tail. Mercedes asked if I needed help with the plug, and I told her, "No," that I could do it. I then shimmied into the tight pink hot pants and turned for her to attach my tail. She then gave me the bikini top from my pink flowery bikini to wear and told me to insert my breast forms. Finally, I slipped on my pink high heels and turned so that Mercedes could apply my makeup, which she did complete with kitten whiskers drawn on. She then fitted my pink wig on my head and topped it off with a pair of kitten ears on a headband. Finally, she attached a pink collar with glitter writing that said, "Sissy." I was imagining what my day was going to be like before she got to the point that she attached the pink leash to my collar and told me to get on the floor so she could deliver me to "Senor Tom."
I was led, on my hands and knees, to the pool where my cheerleader and her quarterback were already having coffee and breakfast. Mercedes walked me to quarterback and handed him my leash. He thanked her and smiled at me. "Good morning kitten. Don't you look cute today!" I thanked him as I sat back onto my haunches, waiting for instructions. He invited me to prepare a plate of food and a cup of coffee, but told me to stay by him on the pool deck, while he and cheerleader enjoyed their breakfast with me by their side. When I finished, quarterback told me to crawl under the table in front of him. I did as he as he told me and once there, I was on my knees face to face with his crotch. His cock was poking out from within the loose fitting shorts he was wearing. I couldn't see quarterback's or my cheerleader's face from where I was, but I could hear their conversation and laughter as they enjoyed a second cup of coffee together. While I waited there, looking at his thick cock, quarterback said, "Kitty. Pull my shorts off." I did as he asked and now was inches away from his growing erection. "Lick it kitty. Take your time. Just lick it." I leaned in and began to slowly and softly lick his cock and balls. All over. I tried to be as kitten-like as I could manage. After I licked him for several minutes, he stood up and walked over to a chaise lounge by the pool, my cheerleader following him. "Come kitty," he said as he walked away. I crawled over behind him and next to his chair. He smiled at me, "Time to earn your cream kitty." Kneeling beside his chaise lounge, I licked him more until he said, "Suck it Sissy." I held him in my manicured fingers and began to take him into my mouth. He'd been in my mouth during the trip already, but only for purposes of me cleaning him off. This time it appeared he wanted me to make him cum, and I was very excited to be doing so. As I became lost in the act, my cheerleader reached over and took her quarterback's cock into her hands and began stroking him into my mouth. "Get ready baby," she cooed. "This is all for you." I began to suck him more fervently as my cheerleader voiced encouragement to me, saying, "That's a good Sissy. Good girl!" Then it happened. The explosion! Quarterback began grunting and I could feel him as he pumped load after load of his thick cream into my mouth. There was so much sperm! He was drooling out of my mouth and onto my chin. When he stopped, he said, "That was good sissy. You are an excellent cocksucker. Now kiss your wife." I looked at her and she was smiling at me, as if she had known all along that this was my test. She leaned over him and kissed me, tasting his cum in my mouth and on my lips. When we stopped, quarterback told me to lie on the lounger next to him, in case he needed me again. As I crawled up onto the chair, I could see Mercedes and Maria standing off in the distance, in the kitchen area watching us. Mercedes caught my eye and winked at me, showing her approval at what she'd seen me do, as if I had cemented for her that I was the genuine article.
We relaxed by the pool for the rest of the day. I sucked off quarterback two more times, once with the help of my cheerleader. On the third time, when I was doing it alone, he came all over my face and then rubbed his spent thick cock all over my face before sending me to get ready for our evening out. After the day I'd spent as their kitten, I was anxious about the evening plans. I had never been out dressed as a woman before, and this experience had me feeling very nervous.
Mercedes came to my bedroom right after I entered. She stood in my doorway looking at me, silent, but her eyes saying everything. She had no idea, until today, just how much of a sissy I was. Seeing me submit to quarterback as I did had impacted her view of me. Then she spoke, "Are you ready to dress for your evening Sissy?" I replied, "Am I?" Mercedes smiled and said, "After today, I believe you are. Yes. Please, shower while I get your outfit organized." I went to the shower and washed off, including a quick shave to make sure I was smooth. When I returned to my bedroom, Mercedes was waiting for me. Lying on the bed was a pink lace lingerie set of French cut panties, a full cup bra, and a lace garter belt. She helped me into them and then helped me fill the bra cups with my largest breast forms. She helped me slip on a pair of black stockings and attached them to my garter straps. Next she had me step into a pair of light blue five-inch high heels. And finally, the dress. I hadn't taken my eye off of it from the moment I saw it lying on my bed. It was a white lace and tulle party dress that would show off my legs in a very revealing and flattering manner, and I do have nice legs. And I have to admit, when shaved smooth as they were during our trip, they looked so so feminine. Next she made up my face in a very pretty and feminine look, including bright, wet red lipstick. She handed me the tube when she finished and said, "Make sure you apply this often tonight Sissy. Senor Tom says he wants your lips to look wet all night." She fastened my hoop earrings on and then had me hold out my hands so she fasten a pearl bracelet on one wrist and a gold bangle bracelet on the other. Finally, she fastened as set of pearls around my neck. And then, last, but not least, she put a dark auburn colored wig on me that was somewhat short and had bangs that made me look very feminine, and very sissy. Mercedes stood back to take me in. "You look very pretty Sissy. Very pretty. Are you ready to join your wife and her man?" I was so nervous. But I nodded and said, "Yes. I am." "Good," she said. “I have one last message for you from Senor Tom. Tonight, you will meet a tall dark stranger. You will submit to him Sissy. He is safe and is not really a stranger. But your wife does not know this. Only you and Senor Tom will know. Do you understand?" I was unsure what she was saying. "He's safe?" I asked. "Yes. He has been tested. He has been chosen by Senor Tom. He is safe." "And I am to do what he asks?" I replied. "Yes Sissy. Whatever he asks." I hesitated, wondering. What all that could mean, but nodded my head. "I understand." Mercedes smiled at me and said, "Have fun Sissy. I will look forward to reading about it on your blog." Mercedes had read my blog? Oh no! She knew everything!
I walked slowly into the main room and found my cheerleader and her quarterback waiting for me. She was stunning, wearing a tight and short silver dress cut low in front, revealing her plump cleavage, and wearing very high heels herself. Quarterback was wearing a pair of dark trousers and a white shirt open at the top. He whistled at me when he saw me. "Sissy!" He exclaimed. "You look ready for a hot night!" My cheerleader was looking at me funny. I don't think she was completely sure about this me going out in public. She asked her quarterback, "Are you sure this club is safe for her tonight?" He laughed. "Yes babe. It is a private club and I have vetted it completely. It is absolutely safe and someone like Sissy will be accepted there. Now, it is time to go. Our car is waiting."
We walked together outside and climbed into the Landcruiser that had transported us from the airport. I was, if I'm honest, beyond nervous. But also, very excited to be given this opportunity to go out dressed as I was to a place where I felt certain that no one would know me. Quarterback's assurances helped too. I trusted him when he said he'd vetted it completely. So far everything he'd done where this trip was concerned seemed designed to keep our secret safe, but permit us to be free to be who we were together in private.
The club we went to was not in the town. We drove quite a ways before our driver turned down a gravel roadway. After driving a bit further on the dark road, we pulled into an opening and there was a large building with a low roofline and only a few windows lit to the outside. We pulled in front and our driver opened the door to help us exit. My cheerleader and I walked on either side of quarterback up to the front door where two men stood by the door. Quarterback showed them a ticket of some kind and the men opened the door for us to enter. When we walked inside it was quite elegant, with subdued lighting. It was basically a private club/restaurant. We were taken to a table in the corner, somewhat close to a Latin music trio that was playing very nice music. We were greeted by a pretty Hispanic waitress who asked for our drink orders. Quarterback took charge and ordered us all Mojitos. When she left, quarterback looked over the menu. Upon her return, he ordered several different things from the menu for us to eat. He toasted us and said, "To a perfect evening. What happens in Mexico, stays in Mexico." We laughed and toasted each other. I was feeling a bit more relaxed, especially after the first few sips of my delicious Mojito. Our waitress brought us another round without anyone asking. We ate and drank and enjoyed the ambiance of the private club. There were beautiful people everywhere. After a while, the trio began playing music suitable for dancing and that is when quarterback said to me, "Why don't you ask your wife to dance Sissy?" I looked at him. "Really? The two of us?" "Yes Sissy. The two of you. I want to watch."
So my cheerleader and I walked together to the dance floor and began dancing. The music was nice and we slowly relaxed and started to get more and more into it. We danced a few songs, each of us casting occasional glances toward quarterback, each time finding him smiling at us from our table. After a few dances, we decided to return. We sat down and shortly after we did, a tall dark stranger approached our table. He introduced himself as "Victor," and asked if he might join us. Quarterback spoke for us as he stood and shook Victor's hand. "Of course! Please!" Quarterback then introduced us to Victor as Susan (my cheerleader but not her real name) and Leeanne. Victor took each of our hands and kissed us in a very gallant manner. He was a true Hispanic gentleman. Our waitress came by our table and Victor ordered a bottle of champagne. He then struck up what sounded like small talk, although I had concluded quickly that he had to be the man Mercedes had referred to earlier. He asked what we were doing in Mexico and that is when quarterback dropped the bomb. He gave a little conspiratorial glance around the club and then said, "The truth?" Victor laughed and said, "Yes! By all means!" Quarterback then looked at my cheerleader and then smiled. "Susan is my ex-wife. And Leeanne is her sissy husband. We're here on vacation together." At the mention of the word sissy in referring to me Victor quickly looked at me and exclaimed, "You are not a woman? It can't be! You look so lovely!" I honestly blushed a deep red. Not just that quarterback had so bluntly outed me, but at Victor's nice reaction. My cheerleader's mouth dropped open in stunned silence. Victor then raised his glass to us and said, "To a unique and special night!" We drank our champagne and chatted about how long we'd been there and where we were staying. I knew that Victor had to know all of this. After a while he looked at me and asked, "May I have the pleasure of a dance with the lovely Leeanne?" My heart fluttered. I thought, no matter what anyone might say about quarterback, I was enjoying this moment. I held my hand out to Victor and replied, "Of course." As I stood to join him on the dance floor my cheerleader was eyeing me like she did not know what was going on. I’m quite certain now that she did not.
The music playing was slow and Victor took control of me, pulling me close to him, my large breast forms pressing firmly against his muscular body. His hand on my back was soon roaming freely and then he was under my dress, cupping my panty covered behind, obviously revealing me to other guests at the club as he spun me around the dance floor. I was feeling so overwhelmed that I was just glad that he was exerting such control. Otherwise, I don't know what I'd have done. When the music stopped he pulled me to him and whispered, "There is something you need to know Leeanne." I asked, "Yes? What?" "I'm enthralled by girls like you. I hope you will permit yourself to become comfortable with me." I looked at him as he watched for my reaction and then moved closer as if to kiss me and, in that moment, my cheerleader and her quarterback's eyes upon me, I let him kiss me on the mouth, and then permitted him to slide his tongue inside as well. He was such a good kisser. He held me as he kissed me with passion on the dance floor. We then walked, hand in hand, back to our table and sat down, where we had another drink. After a few minutes, Victor took my hand from the table and moved it under the table to his crotch where I could feel how excited he was. His cock was quite large and it was clearly hard inside of his trousers. My cheerleader was watching me as I let him hold my hand there. He then leaned close to me and whispered, "Take it our Leeanne." Mercedes’ instructions to me, sent from quarterback, earlier, returned to me. 'Submit to him.' I responded by reaching to locate his zipper and when I did, I tugged on it and pulled it down. I then fumbled with his belt buckle and, after unhooking it, I released the top fastener to his trousers and reached inside of his pants. I was attempting to be casual, but it was obvious what I was doing. And my cheerleader was enraptured as she watched. Once it was out I softly stroked and fondled Victor’s cock. He was so hard and yet so soft and alive. I couldn't believe what I was doing. We were somewhat private at our table in the corner, and thankfully the lights were dim. Victor leaned over and kissed me on the ear and then said, "I want you to suck my cock Leeanne." I looked at him with questioning eyes. He was dead serious. He said, "Here. Now." I looked at my cheerleader and her quarterback. I know neither of them could hear what Victor has said above the music. But in that moment, quarterback gave the most imperceptible nod of his head, as if to say, 'Do it.' And so, right there at the table in the club, while my cheerleader watched me, I scooted out my chair and dipped my head down into Victor's lap and took his cock inside of my mouth and began sucking his dick. Soon, as I bobbed up and down on him, he placed his hand on the back of my head and began directing me, and then he began to moan and I could tell he was going to cum in my mouth. Just then he pushed my mouth down forcing his cock to go deep inside of my mouth, gagging me in the process. I wanted to make sure I got all of his cum in my mouth and so I locked on to him as firmly as possible in preparation for the moment, which hit very quickly. With Victor holding my head down firmly on his cock so that I couldn’t escape if I’d wanted to, and I didn’t, I swallowed every blast he shot into my mouth until he was finished. When he let me lift my head back up above the table, my cheerleader was looking at me with an expression that seemed to say, 'Oh! My! God!' I smiled at her and blushed. After a few minutes Victor stood and announced that it had been a pleasure to meet us and that he hoped to see us again in the future. He then left us there alone to absorb what I'd just done.
Quarterback smiled and said, "Good Sissy. Very good." Then my cheerleader looked at him as it must have just dawned on her. "You knew him! Didn't you?" He laughed. "Of course babe! I wouldn't put her in a situation that I didn't have control over. But wasn't it hot?" She looked at him and gave him a fake angry look. "You fucker! I can't believe you didn't let me in on that!" He laughed and said, "It wouldn't have been as much fun if I had. And I didn't hear her complaining!" I smiled, hearing them talk about me like that. I said, "No. I have no complaints. Actually, it was fun. Thank you." Quarterback smiled and said, "You are quite welcome Sissy. And now, I think it is time to return to our villa. That got me so hot, I think I need to fuck your wife a few times."
We returned to our villa and they went to their room and I went to mine. Lying on my bed was a pretty pink lace babydoll nightie and beside it was a note. It read, “I hope your evening was memorable Sissy. Buenas noches, Mercedes.” It was, without a doubt, an amazing evening that I will never forget. I am now a day behind on my posts. But I'm hoping quarterback will be pleased with my description of Day Three, and not be too mad at me.