One of my most memorable experiences at an ABS has to be my very first time ever. I was 19 almost 20. I had met this woman, she was quite a bit older than me, she was 48 at the time. We had hung out and had sex after the bar (I was in the military) a handful of times. Each time she seemed more and more dominant. Well, I had some vacation time saved up and she told me she wanted to get away for a week. I was able to go. She told me not to even pack a bag, just get dressed and come on. I though this was odd when I got to her place and she had 3 full suitcases. We got to our destination, which I slept so I wasn’t sure where it was. She said she would order something for delivery and for me to take a shower. I got out of the shower and I realized I didn’t have a stitch of clothes to put on. I went downstairs naked and she was sitting on the couch watching me. I could see she was dressed very slutty. I asked her “should I just stay naked all week?” She told me “no, I brought you all the clothes you need.” She pointed to the bedroom, and said “go look on that bed, and put those clothes on and come back out.” I walk back there and all that is there is a set of fishnet thigh highs, hot pink boy short panties, and a hot pink bralette. I was very unsure at first, but I thought she is the most intriguing and fun woman I have ever met, and she has shown me things I never knew existed. So I put them on, and checked myself in the mirror. I walked out and for some reason I felt a little shake in my butt I didn’t know I had. She giggled and said “every single time” she was referring to the first time she dresses a guy and he always shakes his butt in the panties. She told me to come let her see, she decided the black thigh highs needed to be hot pink so she traded me some. Then she gave me a black wrap skirt and she tied and adjusted it until she was satisfied. Then she went looking for a top and found a sheer black crop top so I put it on. She then looked through her wigs, And decided to make me a brunette. She found one with medium length curly hair, and set it aside. Then she had me sit down in front of her and she did my makeup. Then put the wig on me and fixed my hair to have just a little hanging down in front and a loose pony tail on the side. Then she found me some shoes. These were like 3″ platform heels and it took a minute, but i figured them out. They really made my butt “pop”. She had some small breast enhancers and put them in my bralette for some size. She was happy with her work, and took a couple pictures of me. I saw them and couldn’t believe it, I looked like an 18 or 19 year old girl. I mean I even had curves. I didn’t even recognize myself. Just then the doorbell rang, she said “oh, the food is here, be a dear and get it for us? Please.” So I went to the door more nervous than ever. She stopped me and said “remember, no one here knows you, have fun, and just let loose.” So she handed me the money and I opened the door. Standing in front of me was a man in his early 20s full of muscle and I had never even THOUGHT about another man sexually, but this was different. I asked him if he would mind putting the food on the table. For us, and he said he would and walked in. I closed the door behind him, and I had only exact change to give him. I apologized for not having tip money when he grabbed his crotch and said I’m sure you can find another way to tip me. Without even thinking I dropped to my knees and pulled his thick 6″ out and began to eagerly suck it. He didn’t last very long and when he said he was going to cum I pulled his cock out and stroked his cum into my open mouth. It was my first time ever and I was so turned on. He left and I begged to be allowed to cum. She then told me that from now on I am to refer to her as Mommy. So, after we ate, Mommy and I got in the car. We drove for about 5 mins when we pulled into the parking lot of a lingerie store. We went in and shopped around tried a couple things on. She really liked a particular baby doll on me and she bought it. Then she wanted to have some real fun, because she had been careful not to let me talk to loud so everyone thought I was a woman. Well, she picked out three or four items for us both and all of mine were garters, skirts, or short tops. Well, she asked the sales lady if she minded watching us try these on and help decide which ones were the best. Well, Mommy came out first and she was taking her time chatting up the sales girl. So I came out in a couple tops still wearing my bralette. Then I went back in and there was a three piece set. I set the g-string aside and put on the top and the garter. They were black with some hot pink lace trim that was ruffled and looked kinda like a skirt. They fit absolutely perfect, so I made one last check in the mirror to be sure I was completely in my panties and I opened the door. Mommy was blocking the view of the sales girl and her jaw dropped as she wasn’t expecting me to willing expose myself like that. The sales girl gave out a slight giggle and she had a deviant smile come across her sweet face. She said “oh how I adore sissy boys” she asked Mommy if she could have a Little fun with me. Mommy told her to do as she pleased. Well, she first told me she had the perfect skirt and top for my lingerie. She grabbed my hand and interlinked my fingers and rubbed her breast on my arm, and whispered “if you are a good little sissy you will be able to try out my pussy.” I turned and said “Mommy is this ok with you?” She said “you have some fun and your sister will bring you back to me when she is done with you.” That’s when the sales girl took my hand and put it on her panty covered pussy and said “I have always wanted a sissy brother to play with.” So we walked out onto the sales floor, multiple couples and a few groups of girls were browsing and every so often they would notice I only had underwear on and that I was not a girl. The looks and giggles just turned me on that much more. She finally got to the outfit she wanted by taking the longest possible way, and told me I could go ahead and put it on so I did. It didn’t cover much but it did help out. She then held my hand and we looked at everything in that store twice and I will swear to it. She would bend over in front of me and rub her ass on me or she would have me squatting down looking at something on a bottom shelf and she would either bend over in front of me or raise her skirt up showing me how wet her panties were. After she decided she had teased me and everyone else in the store she grabbed a handful of items and we went to the dressing room. This time though I noticed my stuff was neatly folded on a table, and she took her keys out and unlocked the door at the end of the hall. This led into a room that had a couple chairs, couch, and three flat-screen tvs. She shut and locked the door and told me no one else could come in. She then turned on the first TV and it was porn, the second TV were cameras, and the third TV was also cameras. These were the security cameras for the theater and booths. They were actually really high quality for the time. She told me “hey Sissy boy. How about you come over and get your sister naked?” I didn’t waste any time at all and I started at her feet and worked my way up to her panties and stopped. I then took her shirt and bra off. She was a pale, petite redhead, about 5’8″ tall with an A maybe small B cup perky tits. All she had left on was her panties. I said “Will you please, just please stand up for me and walk back and forth shaking your cute ass for me and then will you please take your panties off for me? Please, I have always wanted to see you naked Sis.” She said “I will definitely do that, because I want my brother’s first sissy experience to be perfect.” She walked back and forth and she would bend over slightly and look back at me. Her hips were quite wide for her frame, and her butt didn’t stick out very far, but her thighs were thick and muscular, while her butt bounced with each step. She stopped and she had her back to me and she slid her panties down to her ankles without me being able to see her pussy. She then said “now I need you to close your eyes. I want you to have to take off a blindfold to see your sister’s pussy” she used her panties to make a blindfold and she sat down in front of me with her legs closed and took the blindfold off, she then leaned back and slowly opened her legs. She had a perfectly groomed triangle of red hair above her pussy. I was in love with her perfect body. She then decided to put on a matching set of lingerie to mine and she matched my outfit. Then she asked me to come to the couch and watch some TV with her. She started a movie and said “we have a homemade porn here with the employees.” She said she was going to play it. It was actually really good and some of them were tripod angles, some security, and some handheld by someone else. She said “I want you to lick my pussy sissy boy.” I got down in front of her, but she wanted to sit on my face instead. She was dripping wet when she lowered her pussy on my mouth. She started to ride my face, and was able to make herself cum. When she did this she didn’t get up she just leaned forward and rolled her hips up so I had a perfect view of her pussy and she was gently caressing my dick through my panties. She said “your little dicklet is so cute. No wonder Mommy wants you dressed like a little girl hahaha.” She kept on rubbing me and she knew just when to stop so that I wouldn’t cum. She was having so much fun, and then she decided she wanted to cum again and she sat back up and rode my face to another orgasm. This time she got up, and said “come up here and let’s watch Mommy get gangbanged in the theater.” Sure enough there she was getting on the table in the middle of the room. There were about 5 men around her and she asked for the lights to be on. That also meant to record it. The attendant in the back hit record on the four security cameras and went ahead and grabbed a handheld also. Sister and I watched and we played with ourselves but neither of us came. We were in awe of the sight. After Mommy was done she got up, and said something to the attendant and he walked her to the room we were in. It had a second door that went to the theater office. Mommy walked in and had cum dripping out of her and off of her. I said “Mommy, do you want Sis and me to clean that cum off of you?” She said “Yes, please do babies.” We didn’t even hesitate and began licking her all over. It tasted so good, and when she was happy with the job we did she said “ok, let me sit down. Mommy is tired, but wants to hear what you two have been up to.” Sister said “Well, I have used my Sissy Brother’s face to cum twice, and I have been edging him. I didn’t want him to cum yet.” Mommy asked “Sissy boy, would you like to cum?” I said “Yes Mommy please let me cum.” Mommy told me to lie down on the couch. She then walked over and after she moved my legs she sat down and put them across her lap. She said “Daughter, I want you to sit across from us and watch. If you want to do anything with your Sissy’s cum then I will let you know when it is time. You are allowed to play with yourself and cum if you want.” Mommy then put on some transsexual porn, and began playing with me. She watched me, and sister and told me I could only watch the TV. She had turned the other two off. Then she pulled me out of my panties and she began massaging my dick and would just let go completely to keep me from having an orgasm. Then after what seemed like an eternity she said “Do you want anything to do with your sissy brother’s cum?” She said “I want him to cum in my panties I was wearing earlier.” She then got up and grabbed them and held them over my the head of my dick and I was finally allowed to cum. It was the most intense orgasm of my life, and it felt like it lasted forever. Sister neatly placed her panties to the side and asked Mommy, “I told Sissy that if he was a good boy I would let him have my pussy. Can I please get him hard again and play?” Mommy said “yes, just bring him to the cabin when you are done. I am tired and am going back.” So Sister told me to get up and the couch was a fold out. We folded it out and, we just laid there cuddling watching a movie for a while. She flipped over to the theater and noticed there were three guys that were watching the movie. She said, “come on, get dressed, let’s go have some fun.” So we got dressed, and went to the theater. We walked in and sat beside each other and watched the movie playing. It only took a minute and all three guys came up. Sister said “hey boys, I have to let you know, you are all good looking men, but I’m a size queen. If you don’t measure up then I can’t play with you.” Pointing to me she said “this is my sissy brother and he is my fluffer tonight. He will suck your until you get hard, if I say you can then you come over to me. If not he will finish you because he is a good sissy and we don’t want anyone to go home with blue balls.” They all three got naked and lined up. I said “can we turn the lights on?” I waited and then there was a handheld camera on me and I began to suck the first dick. It was thick and around 8″. She approved and he was over there playing with my sister. Next up was a little bit thinner cock but he was 10″ and he passed. The third one was the thickest cock I had ever seen and he was only 6.5″ but the girth was bigger than a coke can. I tried, but could only stroke him and get the tip. The other two finished before the third walked up. He walked over and asked if she thought she could get it in her mouth. She got the entire head in but said it hurt. I offered to lick the cum out of her pussy but he said that was just extra lube. He told her he would go slow. And he did, until she had the entire thing in and got used to it. She started rocking her hips and Then she got this look in her eyes and she said “Please wreck my sweet little pussy!” And he did. He fucked her hard either on her back or doggy for every bit of an hour. She said “I have to ride this thing” so he laid down and she mounted him and she rode him then turned around and went reverse cowgirl and then she rode him hard begging for his cum. He finally came, and she got off, kissed him, grabbed my hand, and took me back to our room. She asked “Do you want to add your cum to this or lick it first?” I said “I wanted to add to it first.” She then bent over in front of me and I was hard and ready, I am about 6.5″ with a diameter of 1.5″ so I am above average, I went balls deep in my sister for the first time ever and she said “Are you in?” I said “Yeah, sis, I am!” She said “Wow, I can’t even feel you.” She then told me to lie down and she rode my dick nice and slow and made me cum. She then got up and sat on my face saying “Sissy boys always clean up after real men!” Then we got dressed and she told me she knew a shortcut to the cabin. So we walked there hand in hand. We then climbed in bed and cuddled each other right next to Mommy.
Source: reddit.com/r/sexystories/comments/ixhwps/mommy_makes_me_her_sissy_boi_bi_fmf